HCID 10505810, compound → HCID 67674084, compound

HRID 1585512Notes

Reaction equation

HRID 1585512 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]2[C@H:12]([CH2:13][CH2:14][C:15]=1[CH:16]=O)[C@H:11]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]2=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-].[O:28]=[C:29]1[CH:33]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:32][CH2:31][N:30]1[CH2:53][C:54]([F:57])([F:56])[F:55]>O1C(CC)C1>[C:1]([O:5][C:6]([C:8]1[N:9]2[C@H:12]([CH2:13][CH2:14][C:15]=1/[CH:16]=[C:33]1/[C:29](=[O:28])[N:30]([CH2:53][C:54]([F:55])([F:56])[F:57])[CH2:31][CH2:32]/1)[C@H:11]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]2=[O:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10505810HCID 10505810, compoundHCID 58430309HCID 58430309, compound

Product 1

HCID 67674084HCID 67674084, compound

Reagents, catalysts & solvents 1

HCID 78341,2-EpoxybutaneSolvent

Procedure

A mixture of 0.50 g (6R, 7S)-7-tert-butoxycarbonylamino-3-formyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (10) and 0.96 g rac-[2-oxo-1-(2,2,2-trifluoroethyl)-3-pyrrolidinyl]-triphenylphosphonium bromide in 6.0 ml 1,2 epoxybutane was heated to reflux for 6 h. The solvent was evaporated and the residue was purified by chromatography on silica gel using n-hexane:ethyl acetate=3:1 as eluent. The title compound, (E)-(6R, 7S)-7-tert-butoxycarbonylamino-8-oxo-3-[2-oxo-1-(2,2,2-trifluoro-ethyl)-pyrrolidin-3-ylidenemethyl]-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester, was obtained as white foam (0.55 g;78% Th).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. customThe solvent was evaporated
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0c41ee74a1324efd8e7e8ac868120704
Source dataset
uspto-grants-1999_08
Patent number
US05939410

Reaction notes

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