HCID 20786195, compound → (E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1)[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH3:2].[C:24]([O:28][C:29](=[O:42])[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][C:38](=[O:41])[CH:39]=[CH2:40])([CH3:27])([CH3:26])[CH3:25]>>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:16]1[CH:21]=[CH:20][C:19](/[CH:40]=[CH:39]/[C:38](=[O:41])[NH:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[NH:30][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:42])=[CH:18][CH:17]=1)[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH3:2]Participants
Procedure
Key building block (E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester (II) can be prepared according to Scheme 6. Starting with commercially available 2-bromo-ethanol (XXIX), silylation with tert-butyldimethylsilyl chloride provides (2-bromo-ethoxy)-tert-butyl-dimethyl-silane (XXX). Alkylation of the potassium enolate of (4-bromo-phenyl)-acetic acid ethyl ester with XXX furnishes 2-(4-bromo-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester (XXXI). Heck reaction of XXXI with (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester gives key building block 2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-hydroxy-butyric acid ethyl ester (II).
Sources & evidence
- ORD record
- ord-d4346a0ab3f34bd1992000247c2a84fc
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202866B2
Reaction notes
Loading…