[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol → HCID 57978239, compound

HRID 1866526Notes

Reaction equation

HRID 1866526 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:16]Br)=[CH:11][C:10]=1[CH2:26][OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([O:30][C:31](=[O:44])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][C:40]([NH2:43])([CH3:42])[CH3:41])[CH:34]=1)[CH3:29]>>[CH2:28]([O:30][C:31](=[O:44])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][C:40]([NH:43][CH2:16][C@@H:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]([CH2:26][OH:27])[CH:11]=2)[O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])([CH3:41])[CH3:42])[CH:34]=1)[CH3:29]

Participants

3

Reactant 2

HCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanolHCID 56840061Ethyl [3-(2-amino-2-methylpropyl)phenyl]acetate

Product 1

HCID 57978239HCID 57978239, compound

Procedure

Prepared according to the procedure used for preparation 22 using [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol (Preparation 23) and [3-(2-amino-2-methyl-propyl)-phenyl]-acetic acid ethyl ester (Preparation 47) to give the title compound as a yellow oil. 1H NMR (400 MHz, CD3OD): δ=7.48-7.05 (11H, m), 7.04-6.96 (1H, d), 5.10 (2H, s), 4.80-4.74 (1H, m), 4.78-4.63 (2H, q), 4.16-4.05 (2H, q), 3.60 (2H, s), 2.89-2.63 (2H, m), 2.70-2.62 (2H, m), 1.24-1.20 (3H, t), 1.07-1.04 (6H, d), 0.81 (9H, s), 0.00 (3H, s), -0.18 (3H, s) ppm. LRMS (electrospray): m/z [M+H]+ 606, [M−H]− 604.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8e4feb4ff89a483ca6f904af71894e44
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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