Benzyloxycarbonylglycine → 3-(2-Benzyloxycarbonylamino-acetylamino)-benzoic acid methyl ester
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1.[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])=[CH:15][CH:14]=1>>[CH3:2][O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:25](=[O:26])[CH2:24][NH:23][C:21]([O:20][CH2:19][C:16]2[CH:15]=[CH:14][CH:13]=[CH:18][CH:17]=2)=[O:22])[CH:6]=1Participants
3
Procedure
3-Amino-benzoic acid methyl ester hydrochloride (1.88 g, 10.0 mmol) was reacted with N-α-CBZ-glycine (3.14 g, 15.0 mmol) according to the procedure of Example 102, step a to afford the product (3.12 g, 91%). 1H NMR (300MHZ, CDCl3) 10.18 (1H, br s), 8.26 (1H, m), 7.84 (1H, d), 7.65 (1H, d), 7.55 (1H, d), 7.48-7.22 (7H, m), 5.05 (2H, s), 3.85 (3H, s), 3.83 (2H, d).
Sources & evidence
- ORD record
- ord-86c2e0a9202b4c11bc83554998c86565
- Source dataset
- uspto-grants-2002_11