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

HRID 370501

Reaction equation

HRID 370501 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][CH3:17])=[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][CH3:17])=[O:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 20275793Methyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

Product 1

HCID 20275792Methyl 3-acetylthio-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylateYield 61.5%

Reagents, catalysts & solvents 1

HCID 71583Chloroform-DSolvent

Procedure

0.064 g of methyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate was dissolved in 1 ml of deuterochloroform and 0.063 g of triphenylphosphine added. TLC and NMR analysis indicated complete conversion of starting material to product. The crude product was chromatographed on silica gel using ethyl acetate/hexane as eluant to give 0.035 g (61%) of purified product.

Workup

  1. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-2737ef72fd19415787d4973fe8274dbf
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Linked notes

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