(3S,4S)-1-[1-(allyloxycarbonyl)-1-(triphenylphosphoranediyl)methyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine → allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464728Notes

Reaction equation

HRID 1464728 reaction equation
[CH2:1]([O:4][C:5]([C:7]([N:27]1[C@H:30]([C@H:31]([C:33]([S:35][CH3:36])=S)[CH3:32])[C@@H:29]([C@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH3:38])[C:28]1=[O:47])=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1>[Si:40]([O:39][C@@H:37]([C@H:29]1[C:28](=[O:47])[N:27]2[C@@H:30]1[C@@H:31]([CH3:32])[C:33]([S:35][CH3:36])=[C:7]2[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH3:38])([C:43]([CH3:45])([CH3:44])[CH3:46])([CH3:41])[CH3:42]

Participants

3

Reactant 1

HCID 86747783(3S,4S)-1-[1-(allyloxycarbonyl)-1-(triphenylphosphoranediyl)methyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

Product 1

HCID 57185440allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (3S,4S)-1-[1-(allyloxycarbonyl)-1-(triphenylphosphoranediyl)methyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine (325 mg) in toluene (3 ml) was heated under reflux for 4.5 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography [ethyl acetate-hexane (1:3, V/V)] to afford allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (164 mg).

Workup

  1. temperatureunder reflux for 4.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography [ethyl acetate-hexane (1:3, V/V)]

Sources & evidence

ORD record
ord-b4ccb5f9c30d40ffadeb0fb2803aa4d7
Source dataset
uspto-grants-1994_04
Patent number
US05306816

Reaction notes

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