3-{2-[(2R)-2-(tert-butyldimethyl silanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid → 3-[2-({(2R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methyl propyl]-N-[2-(4-chlorophenyl)ethyl]-N-ethylbenzamide
Reaction equation
[Si:1]([O:8][C@H:9]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][OH:33])[CH:26]=1)[CH2:10][NH:11][C:12]([CH3:24])([CH3:23])[CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](O)=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][NH:44][CH2:45][CH3:46])=[CH:38][CH:37]=1>>[Si:1]([O:8][C@H:9]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][OH:33])[CH:26]=1)[CH2:10][NH:11][C:12]([CH3:24])([CH3:23])[CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([N:44]([CH2:43][CH2:42][C:39]1[CH:38]=[CH:37][C:36]([Cl:35])=[CH:41][CH:40]=1)[CH2:45][CH3:46])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 3-{2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxy methyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid (preparation 37) and [2-(4-chloro-phenyl)-ethyl]-ethyl-amine hydrochloride (preparation 81), using a similar method to that of preparation 109, as a white solid in 43% yield. 1H NMR (400 MHz, CD3OD) 7.90-6.90 (10H, m), 6.72 (1H, d), 4.69 (1H, m), 4.63 (2H, m), 3.70 (1H, m), 3.61 (1H, m), 3.49 (1H, m), 3.10 (1H, m), 3.03-2.58 (6H, m), 1.29-1.26, 1.07-1.01 (9H, 2×m), 0.82 (9H, s), 0.01 (3H, s), -0.18 (3H, s) ppm; LRMS APCI m/z 639 [M+H]+
Workup
- customof preparation 109
Sources & evidence
- ORD record
- ord-bacb92d44b1045e9b86da58fee433ff7
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629358B2
Reaction notes
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