2-Bromoethanol → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 220164Notes

Reaction equation

C(OC(=O)C(C1C=CC(/C=C/C(=O)NC2C=CC=CC=2NC(OC(C)(C)C)=O)=CC=1)[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])C.[Br:42]CCO.[Si](Cl)(C(C)(C)C)(C)C>>[Br:42][CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

Reactant 3

HCID 108982-Bromoethanol

HCID 28928tert-Butyldimethylsilyl chloride

HCID 59238281(E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

Product 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

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-9ea18af03a8d41e58c8c60f2461bf5be
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202866B2

Reaction notes

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