Triethylamine → HCID 59201592, compound

Reaction equation

Cl.[NH2:2][CH2:3][C@@H:4]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:5]([O:7][CH3:8])=[O:6].CCN(CC)CC.[Cl:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32]>CO>[CH2:13]([O:12][C:10]([NH:9][C@H:4]([CH2:3][NH:2][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][Cl:27])[C:5]([O:7][CH3:8])=[O:6])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Procedure

A solution of (R)-methyl 3-amino-2-(benzyloxycarbonylamino)propanoate hydrochloride (4.0 g, 0.014 mol) in methanol (80 mL) was cooled to 0° C. To this mixture was added Et3N (3.3 g, 31 mmol), followed by 4-chlorobutanoyl chloride (2.3 g, 15.0 mmol). The reaction mixture was allowed to warm to rt and stirred for 4 h. The reaction was quenched with saturated brine (200 mL), the organic layer extracted with CH2Cl2, washed with 1N HCl, saturated brine, dried over MgSO4 and concentrated to give crude (R)-methyl 2-(benzyloxycarbonylamino)-3-(4-chlorobutanamido)propanoate (5.0 g) that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 7.45-7.35 (m, 5H) 6.01 (s, 1H), 5.84 (d, 1H), 5.11 (d, 2H), 4.42 (t, 5H), 3.68-3.50 (m, 6H), 2.32 (t, 2H), 2.08 (t, 2H).