Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate → benzyl 4-[(2RS)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate

HRID 1719287Notes

Reaction equation

HRID 1719287 reaction equation
[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]=O)[CH2:10][C:9]1=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(=[CH:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Si:1]([N:8]1[C:9](=[O:15])[CH2:10][CH:11]1[CH2:12][CH:13]=[CH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetateHCID 128047181-(t-Butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinone

Product 1

HCID 53904921benzyl 4-[(2RS)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoateYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (4RS)-1-(tert-butyl-dimethylsilyl)-4-(2-oxoethyl)-2-oxoazetidine (240 mg) and benzyl triphenylphosphoranylidene-acetate (521 mg) in dichloromethane (5 ml) was heated under refluxing for one hour. After removal of the solvent, the residue was chromatographed on silica gel (7 g) eluting with a mixture of dichloromethane and acetone (50:1) to give benzyl 4-[(2RS)-1-(tert-butyl-dimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate (373 mg) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for one hour
  3. customAfter removal of the solvent
  4. customthe residue was chromatographed on silica gel (7 g)
  5. washeluting with a mixture of dichloromethane and acetone (50:1)

Sources & evidence

ORD record
ord-d72e58312e914ab881f83889811ba089
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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