Triphenylphosphine → HCID 54520965, compound

HRID 1710250Notes

Reaction equation

HRID 1710250 reaction equation
[N+:1]([C:4]1[CH:42]=[CH:41][C:7]([CH2:8][O:9][C:10](=[O:40])[CH:11]([N:13]2[CH:16]([S:17][C:18](=[O:36])[CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)=[O:24])[CH:15]([CH2:37][CH3:38])[C:14]2=[O:39])Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:43]1([P:49]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O1CCCC1.C(Cl)Cl>[N+:1]([C:4]1[CH:42]=[CH:41][C:7]([CH2:8][O:9][C:10](=[O:40])[C:11]([N:13]2[CH:16]([S:17][C:18](=[O:36])[CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)=[O:24])[CH:15]([CH2:37][CH3:38])[C:14]2=[O:39])=[P:49]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 53951214HCID 53951214, compound

Product 1

HCID 54520965HCID 54520965, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The resulting crude 2-[3-ethyl-4-(4-p-nitrobenzyloxycarbonylaminobutyrylthio)-2-oxoazetidin- 1-yl]-2-chloroacetic acid p-nitrobenzyl ester is dissolved in a minimum amount of tetrahydrofuran, 9 g of triphenylphosphine are added and the mixture is stirred overnight at room temperature under nitrogen. The reaction mixture is diluted with 250 ml of methylene chloride, washed with saturated aqueous sodium bicarbonate solution, dried and concentrated by evaporation in vacuo. The residue is chromatographed over silica gel with toluene/ethyl acetate (1:1) and yields the title compound with the following physico-chemical properties:

Workup

  1. additionare added
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. customdried
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe residue is chromatographed over silica gel with toluene/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-b21eae0e69cb42fe8dccbba20e077fa2
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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