Triphenylphosphine → 2-[(3S,4R)-4-(2-p-nitrobenzyloxycarbonylaminoethylthiothiocarbonylthio)-3-methoxy-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid p-nitrobenzyl ester

HRID 1710253Notes

Reaction equation

HRID 1710253 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:46]=[CH:45][C:11]([CH2:12][O:13][C:14](=[O:44])[CH:15]([N:17]2[C@H:20]([S:21][C:22]([S:24][CH2:25][CH2:26][NH:27][C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])=[S:23])[C@@H:19]([O:41][CH3:42])[C:18]2=[O:43])O)=[CH:10][CH:9]=1)([O-:7])=[O:6].[C:47]1([P:53]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[N+](C1C=CC(COC(=O)C(N2[C@H](SC(SCCNC(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=S)[C@@H](OC)C2=O)Cl)=CC=1)([O-])=O>O1CCCC1.C(N(CC)CC)C>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14](=[O:44])[C:15]([N:17]2[C@H:20]([S:21][C:22]([S:24][CH2:25][CH2:26][NH:27][C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])=[S:23])[C@@H:19]([O:41][CH3:42])[C:18]2=[O:43])=[P:53]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)=[CH:45][CH:46]=1)([O-:7])=[O:6]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 24386Thionyl ChlorideHCID 566154492-[(3S,4R)-4-(2-p nitrobenzyloxycarbonylaminoethylthiothiocarbonylthio)-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl esterHCID 570565232-[(3S,4R)-4-(2-p-nitrobenzyloxycarbonylaminoethylthiothiocarbonylthio)-3-methoxy-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester

Product 1

HCID 566256552-[(3S,4R)-4-(2-p-nitrobenzyloxycarbonylaminoethylthiothiocarbonylthio)-3-methoxy-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid p-nitrobenzyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Procedure

Analogously to Example 24, 0.12 ml of thionyl chloride and 0.23 ml of triethylamine in 0.23 ml of absolute tetrahydrofuran are added to a solution of 640 mg of 2-[(3S,4R)-4-(2-p-nitrobenzyloxycarbonylaminoethylthiothiocarbonylthio)-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester in 4.5 ml of absolute tetrahydrofuran. After reacting and working up, 0.54 g of triphenylphosphine is added to the crude 2-[(3S,4R)-4-(2-p-nitrobenzyloxycarbonylaninoethylthiothiocarbonylthio)-3-methoxy-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester, obtained as intermediate, in 1.15 ml of absolute tetrahydrofuran. After working up and chromatography over silica gel, the title compound is obtained.

Sources & evidence

ORD record
ord-32e0c55302bb4c50a55e1ac9a505e051
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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