methyl 3-amino-5-chlorobenzoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: HATU, 38 mg (0.1 mmol), 14 mg (0.1 mmol) of HOAt, 30 mg (0.1 mmol) of Boc-Glu-OtBu hydrochloride, 0.014 ml (0.1 mmol) of triethylamine and 1 ml of dichloromethane were added to 30 mg (0.1 mmol) of methyl 5-chloro-3-aminobenzoate. The mixture was stirred at room temperature overnight.

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

実験手順: 38 mg (0.1 mmol) of HATU, 14 mg (0.1 mmol) of HOAt, 30 mg (0.1 mmol) of Boc-Glu-OtBu hydrochloride, 0.014 mL (0.1 mmol) of triethylamine and 1 mL of dichloromethane were added to 30 mg (0.1 mmol) of methyl 5-chloro-3-aminobenzoate, and stirred at room temperature overnight.

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

実験手順: HATU, 38 mg (0.1 mmol), 14 mg (0.1 mmol) of HOAt, 30 mg (0.1 mmol) of Boc-Glu-OtBu hydrochloride, 0.014 ml (0.1 mmol) of triethylamine and 1 ml of dichloromethane were added to 30 mg (0.1 mmol) of methyl 5-chloro-3-aminobenzoate. The mixture was stirred at room temperature overnight.

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

実験手順: HATU, 38 mg (0.1 mmol), 14 mg (0.1 mmol) of HOAt, 30 mg (0.1 mmol) of Boc-Glu-OtBu hydrochloride, 0.014 ml (0.1 mmol) of triethylamine and 1 ml of dichloromethane were added to 30 mg (0.1 mmol) of methyl 5-chloro-3-aminobenzoate. The mixture was stirred at room temperature overnight.

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 38 mg (0.1 mmol) of HATU, 14 mg (0.1 mmol) of HOAt, 30 mg (0.1 mmol) of Boc-Glu-OtBu hydrochloride, 0.014 mL (0.1 mmol) of triethylamine and 1 mL of dichloromethane were added to 30 mg (0.1 mmol) of methyl 5-chloro-3-aminobenzoate, and stirred at room temperature overnight.

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

実験手順: 38 mg (0.1 mmol) of HATU, 14 mg (0.1 mmol) of HOAt, 30 mg (0.1 mmol) of Boc-Glu-OtBu hydrochloride, 0.014 mL (0.1 mmol) of triethylamine and 1 mL of dichloromethane were added to 30 mg (0.1 mmol) of methyl 5-chloro-3-aminobenzoate, and stirred at room temperature overnight.

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

実験手順: A mixture solution of 3-amino-5-chloro-benzoic acid methyl ester (21 g, 113.2 mmol), 3-bromo-benzaldehyde (21 g, 113.2 mmol) and p-toluenesulfonic acid (431 mg, 2.2 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 3-[(3-bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl ester (39.8 g, quant.) as a pale-white solid: MS calcd. for C15H11BrClNO2 353.62, obsd. (ESI+) [(M+H)+]351.9 & 353.9. to reflux for 12 hours The solvent was removed in vacuo the residue was washed with ether

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

実験手順: To a stirred solution of 3-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropwise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-5-chloro-benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8ClNO2 (M+H)+: 186.61, observed: 185.9. Then the mixture solution was refluxed for 12 hours Then the reaction mixture was concentrated in vacuo the residue was dissolved in ethyl acetate (500 mL) washed with saturated aqueous sodium bicarbonate solution (3×100 mL) dried over anhydrous sodium sulfate concentrated in vacuo