Ethyl diazoacetate → [2-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester

HRID 221703Notes

Reaction equation

HRID 221703 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[C:9]([O:13][C:14](=[O:30])[NH:15][C:16]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=1)([CH2:21][OH:22])[C:17]([F:20])([F:19])[F:18])([CH3:12])([CH3:11])[CH3:10]>C(Cl)Cl>[CH2:7]([O:6][C:4](=[O:5])[CH2:3][O:22][CH2:21][C:16]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=1)([NH:15][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:30])[C:17]([F:18])([F:19])[F:20])[CH3:8]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 66665702[1-(3-Bromo-phenyl)-2,2,2-trifluoro-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 66666311[2-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propoxy]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

With the use of a syringe pump a solution of 1.87 ml (15.17 mmol) ethyl diazoacetate in 8 ml DCM were added to a stirred solution of 2.01 g (5.23 mmol) [1-(3-bromo-phenyl)-2,2,2-trifluoro-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester and 46 mg (0.105 mmol) Rh2 (OAc)2 in 34 ml DCM over a period of 3.5 h. After 30 min the mixture was evaporated and chromatographed on silica gel (c-hexane/0-20% TBME) to give the desired product contaminated with a diazo ester oligomer.

Workup

  1. customAfter 30 min the mixture was evaporated
  2. customchromatographed on silica gel (c-hexane/0-20% TBME)

Sources & evidence

ORD record
ord-fc57a4f0672646e7884318396d3dafcd
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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