tert-butyl N-[4-(chloromethyl)phenyl]carbamate

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: Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).

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

実験手順: Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).

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 tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H). The resulting reaction mixture quenched with water (25 mL) The aqueous layer was extracted with dichloromethane (50 mL) the organic layer was dried over sodium sulfate filtered concentrated in vacuo

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 tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H). The resulting reaction mixture quenched with water (25 mL) The aqueous layer was extracted with dichloromethane (50 mL) the organic layer was dried over sodium sulfate filtered concentrated in vacuo

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

実験手順: Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).

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 tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)-phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H). The resulting reaction mixture quenched with water (25 mL) The aqueous layer was extracted with dichloromethane (50 mL) the organic layer was dried over sodium sulfate filtered concentrated in vacuo

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

実験手順: Following the procedure as described in Example 50, making variations as required to replace (2-bromoethoxy)(tert-butyl)dimethylsilane with tert-butyl 4-(chloromethyl)phenylcarbamate to react with ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate, the title compound was obtained as an off-white solid in 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.2 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 6.49 (br s, 1H), 6.14 (s, 1H), 4.41 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 3.81-3.73 (m, 2H), 3.45-3.37 (m, 2H), 2.49 (s, 3H), 1.51 (s, 9H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 482.5 (M+23).

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 tert-butyl 4-(hydroxymethyl)phenylcarbamate (0.50 g, 2.24 mmol) in dichloromethane was added pyridine (3 drops), followed by the dropwise addition of thionyl chloride (0.35 mL, 4.98 mmol). The resulting reaction mixture was stirred for 30 minutes, and then quenched with water (25 mL). The aqueous layer was extracted with dichloromethane (50 mL), and the organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford tert-butyl 4-(chloromethyl)phenylcarbamate as an orange solid in 50% yield (0.27 g, 50%): 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 6.51 (br s, 1H), 4.55 (s, 2H), 1.52 (s, 9H). The resulting reaction mixture quenched with water (25 mL) The aqueous layer was extracted with dichloromethane (50 mL) the organic layer was dried over sodium sulfate filtered concentrated in vacuo