benzyl 5-aminopentanoate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl N-Boc-5-aminovalerate (4 g) thus obtained in TFA (50 ml) was stirred at room temperature for 20 minutes. After the TFA was removed in vacuo, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The separated ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford 2.7 g of benzyl 5-aminovalerate. After the TFA was removed in vacuo, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added The separated ethyl acetate layer was dried over anhydrous sodium sulfate The solvent was removed in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl N-Boc-5-aminovalerate (4 g) thus obtained in TFA (50 ml) was stirred at room temperature for 20 minutes. After the TFA was removed in vacuo, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The separated ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford 2.7 g of benzyl 5-aminovalerate. After the TFA was removed in vacuo, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added The separated ethyl acetate layer was dried over anhydrous sodium sulfate The solvent was removed in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Boc-Gly-Gly-Phe-Gly-OH (SEQ ID NO. 1) (575 mg), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the solution was stirred for 30 minutes. The resulting solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred at room temperature for three days. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 560 mg of Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOBzl (SEQ ID NO. 1). The Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOBzl (SEQ ID NO. 1) (560 mg) was dissolved in methanol (60 ml) containing 50% of water, and the solution was added with 5% Pd—C (water content; 50%, 1.5 g) and stirred overnight under hydrogen at ordinary pressure. After the catalyst was removed from the reaction mixture by filtration, the mixture was concentrated to dryness to obtain 300 mg of Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOH (SEQ ID NO. 1). the mixture was stirred at room temperature for three days The reaction mixture was concentrated the residue was purified by column chromatography (CH2Cl2:MeOH=20:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Boc-Gly-Gly-Phe-Gly-OH (SEQ ID NO. 1) (575 mg), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the solution was stirred for 30 minutes. The resulting solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred at room temperature for three days. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 560 mg of Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOBzl (SEQ ID NO. 1). The Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOBzl (SEQ ID NO. 1) (560 mg) was dissolved in methanol (60 ml) containing 50% of water, and the solution was added with 5% Pd—C (water content; 50%, 1.5 g) and stirred overnight under hydrogen at ordinary pressure. After the catalyst was removed from the reaction mixture by filtration, the mixture was concentrated to dryness to obtain 300 mg of Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOH (SEQ ID NO. 1). the mixture was stirred at room temperature for three days The reaction mixture was concentrated the residue was purified by column chromatography (CH2Cl2:MeOH=20:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Boc-Gly-Gly-Phe-Gly-OH (SEQ ID NO. 1) (575 mg), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the solution was stirred for 30 minutes. The resulting solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred at room temperature for three days. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 560 mg of Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOBzl (SEQ ID NO. 1). The Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOBzl (SEQ ID NO. 1) (560 mg) was dissolved in methanol (60 ml) containing 50% of water, and the solution was added with 5% Pd—C (water content; 50%, 1.5 g) and stirred overnight under hydrogen at ordinary pressure. After the catalyst was removed from the reaction mixture by filtration, the mixture was concentrated to dryness to obtain 300 mg of Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOH (SEQ ID NO. 1). the mixture was stirred at room temperature for three days The reaction mixture was concentrated the residue was purified by column chromatography (CH2Cl2:MeOH=20:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Boc-y-Gly-Gly-Phe-OH (575 mg) (SEQ ID NO. 8), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the mixture was stirred for 30 minutes. The solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred for 3 days at room temperature. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO. 8). The Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (SEQ ID NO. 8) (380 mg) was dissolved in methanol containing 50% of water (20 ml), and the solution was added with 5% Pd—C (water content; 50%, 300 mg) and stirred overnight under hydrogen at ordinary pressure. The catalyst in the reaction mixture was removed by filtration, and the filtrate was concentrated to dryness to obtain Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOH (SEQ ID NO. 8) (330 mg). the mixture was stirred for 3 days at room temperature The reaction mixture was concentrated the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO stirred overnight under hydrogen at ordinary pressure The catalyst in the reaction mixture was removed by filtration the filtrate was concentrated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Boc-y-Gly-Gly-Phe-OH (575 mg) (SEQ ID NO. 8), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the mixture was stirred for 30 minutes. The solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred for 3 days at room temperature. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO. 8). The Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (SEQ ID NO. 8) (380 mg) was dissolved in methanol containing 50% of water (20 ml), and the solution was added with 5% Pd—C (water content; 50%, 300 mg) and stirred overnight under hydrogen at ordinary pressure. The catalyst in the reaction mixture was removed by filtration, and the filtrate was concentrated to dryness to obtain Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOH (SEQ ID NO. 8) (330 mg). the mixture was stirred for 3 days at room temperature The reaction mixture was concentrated the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO stirred overnight under hydrogen at ordinary pressure The catalyst in the reaction mixture was removed by filtration the filtrate was concentrated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Boc-Gly-Gly-Phe-Gly-OH (SEQ ID NO. 1) (575 mg), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the solution was stirred for 30 minutes. The resulting solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred at room temperature for three days. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 560 mg of Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOBzl (SEQ ID NO. 1). The Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOBzl (SEQ ID NO. 1) (560 mg) was dissolved in methanol (60 ml) containing 50% of water, and the solution was added with 5% Pd—C (water content; 50%, 1.5 g) and stirred overnight under hydrogen at ordinary pressure. After the catalyst was removed from the reaction mixture by filtration, the mixture was concentrated to dryness to obtain 300 mg of Boc-Gly-Gly-Phe-Gly-NH—(CH2)4—COOH (SEQ ID NO. 1). the mixture was stirred at room temperature for three days The reaction mixture was concentrated the residue was purified by column chromatography (CH2Cl2:MeOH=20:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Boc-Gly-Gly-Gly-Phe-OH (575 mg) (SEQ ID NO. 8), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the mixture was stirred for 30 minutes. The solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred for 3 days at room temperature. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO. 8). The Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (SEQ ID NO. 8) (380 mg) was dissolved in methanol containing 50% of water (20 ml), and the solution was added with 5% Pd—C (water content; 50%, 300 mg) and stirred overnight under hydrogen at ordinary pressure. The catalyst in the reaction mixture was removed by filtration, and the filtrate was concentrated to dryness to obtain Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOH (SEQ ID NO. 8) (330 mg). the mixture was stirred for 3 days at room temperature The reaction mixture was concentrated the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO stirred overnight under hydrogen at ordinary pressure The catalyst in the reaction mixture was removed by filtration the filtrate was concentrated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of benzyl N-Boc-5-aminovalerate (4 g) thus obtained in TFA (50 ml) was stirred at room temperature for 20 minutes. After the TFA was removed in vacuo, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The separated ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford 2.7 g of benzyl 5-aminovalerate. After the TFA was removed in vacuo, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added The separated ethyl acetate layer was dried over anhydrous sodium sulfate The solvent was removed in vacuo