Triphenylphosphine → HCID 13578044, compound

HRID 1788839Notes

Reaction equation

HRID 1788839 reaction equation
C(S([CH:6]1[N:9]([CH:10]([C:24]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[S:25])[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:33])[CH2:7]1)=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[O:33]=[C:8]1[N:9]2[CH:6]([S:25][C:24]([O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[C:10]2[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[O:12])[CH2:7]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 13578043HCID 13578043, compound

Product 1

HCID 13578044HCID 13578044, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1550 mg of 4-nitrobenzyl 2-(4-allylsulphinylazetidin-2-on-1-yl)-3-phenoxy-3-thioxo-propanate (containing 10% pivalic acid), 808 mg of triphenylphosphine and dioxan was heated under an argon atmosphere at 110° C. for 15 minutes. The mixture was evaporated in vacuo to dryness, and the resulting oil was chromatographed on silica gel. Elution with ethyl acetate-hexane mixtures afforded 219 mg of a solid. This was taken up in ethyl acetate and extracted with sodium bicarbonate to afford, after evaporation in vacuo, 192 mg of the title compound (11% of the theoretical yield).

Workup

  1. customThe mixture was evaporated in vacuo to dryness
  2. customthe resulting oil was chromatographed on silica gel
  3. washElution with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-8210441576984f24a7766ee8b616321d
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

Loading…