Triphenylphosphine → Pivaloyloxymethyl 3-acetylthio-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

HRID 1980634Notes

Reaction equation

HRID 1980634 reaction equation
[C:1]([S:4][C:5]1[S:12]S[CH:10]2[N:7]([C:8](=[O:13])[CH2:9]2)[C:6]=1[C:14]([O:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:15])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[2H]C(Cl)(Cl)Cl>[C:1]([S:4][C:5]1[S:12][CH:10]2[N:7]([C:8](=[O:13])[CH2:9]2)[C:6]=1[C:14]([O:16][CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 20275776Pivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

Product 1

HCID 20275786Pivaloyloxymethyl 3-acetylthio-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 71583Chloroform-DSolvent

Procedure

To a solution of 22 mg of pivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate in deuterochloroform were added 14.7 mg of triphenylphosphine. TLC analysis indicated complete conversion of the starting material and the product was shown by IR and NMR analysis to be the title compound. This product was isolated by chromatography on silica gel using ethyl acetate/hexane mixtures as solvent. The yield of product was 13 mg (65%).

Sources & evidence

ORD record
ord-db44d76cee2f4e4daccdfa17c41044b3
Source dataset
uspto-grants-1985_04
Patent number
US04510086

Reaction notes

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