Triphenylphosphine → HCID 14074731, compound

HRID 986225Notes

Reaction equation

HRID 986225 reaction equation
[C:1]1([C:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:8][CH:9]2[N:12]([CH:13]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])Cl)[C:11](=[O:25])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:38]1([P:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C=O)C>[C:1]1([C:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:8][CH:9]2[N:12]([C:13]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])=[P:44]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:11](=[O:25])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 14074730HCID 14074730, compound

Product 1

HCID 14074731HCID 14074731, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(triphenylmethylthio)-1-(benzyloxycarbonylchloromethyl)azetidin-2-one (850 mg), triphenylphosphine (640 mg) and 2,6-butidine (210 μl) in DMF (50 ml) was heated at 80° C. under nitrogen for 24 hours. The reaction was then cooled, diluted with ice water and extracted with ethyl acetate (2×100 ml). The ethyl acetate extracts were washed with water and brine, dried (Na2SO4) and evaporated. The residue was flash chromatographed with a solvent gradient of 15 to 60% ethyl acetate/hexane to afford recovered starting material (500 mg) and then 4-(triphenylmethylthio)-1-[(benzyloxycarbonyl)triphenylphosphoranylidenemethyl]azetidin-2-one (650 mg) as a white foam, Rf =0.20 (30% ethyl acetate/hexane).

Workup

  1. temperatureThe reaction was then cooled
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe ethyl acetate extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customchromatographed with a solvent gradient of 15 to 60% ethyl acetate/hexane
  7. customto afford
  8. customrecovered

Sources & evidence

ORD record
ord-3b78c21aeecd4b7cae11411c0dfd41ce
Source dataset
uspto-grants-1987_12
Patent number
US04711886

Reaction notes

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