Water → Tert-butyl (r)-4-fluoro-3-[[[n-(benzyloxycarbonyl)serinyl]-phenethylamino]methyl]benzoate
Reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH2:15][NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:25]([O:32][C:33]([NH:35][C@@H:36]([C:39](O)=[O:40])[CH2:37][OH:38])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1C=CC2N(O)N=NC=2C=1.O.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH2:15][N:16]([C:37](=[O:38])[C@@H:36]([CH2:39][OH:40])[NH:35][C:33]([O:32][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:34])[CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
8
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
According to the procedure of Preparation 4(c), except using tert-butyl 4-fluoro-3-[(phenethylamino)methyl]benzoate (5.00 g, 15.2 mmole), N-(benzyloxycarbonyl)-D-serine (3.83 g, 16 mmole), HOBt.H2O (2.16 g, 16 mmole), Et3N (2.24 mL, 16 mmole), EDC.HCl (3.07 g, 16 mmole), and 1:1 DMF/CH2Cl2 (75 mL), the title compound (3.44 g, 41%) was prepared as a thick oil following flash chromatography on silica gel (40% EtOAc/hexanes): 1H NMR (300 MHz, DMSO-d6) mixture of amide rotamers δ 7.31-8.18 (m, 2 H), 7.19-7.29 (m, 11 H), 4.86-5.11 (m, 4 H), 4.33-4.79 (m, 3 H), 3.49-3.80 (m, 4 H), 1.51 (s, 9 H).
Sources & evidence
- ORD record
- ord-6f9b9a0a5d2e4512a8a83ad909d63a38
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06503903B1
Reaction notes
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