Triphenylphosphine → HCID 86749091, compound

HRID 128505Notes

Reaction equation

HRID 128505 reaction equation
C([O:4][C:5]([C:7](=[C:27]1[S:31][CH2:30][CH2:29][S:28]1)[C:8]([NH:10][C@@H:11]1[C:25](=[O:26])[N:13]2[CH:14]([C:19]([O:21]CC=C)=[O:20])[C:15]([CH3:18])([CH3:17])[S:16][C@H:12]12)=[O:9])=[O:6])C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+:61].C(OCC)(=O)C>CN(C)C=O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:5]([C:7](=[C:27]1[S:28][CH2:29][CH2:30][S:31]1)[C:8]([NH:10][C@@H:11]1[C:25](=[O:26])[N:13]2[CH:14]([C:19]([O-:21])=[O:20])[C:15]([CH3:18])([CH3:17])[S:16][C@H:12]12)=[O:9])([O-:6])=[O:4].[Na+:61].[Na+:61]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 86749088HCID 86749088, compoundHCID 86749093HCID 86749093, compound

Product 1

HCID 86749091HCID 86749091, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl 6β-[(allyloxycarbonyl)(1,3-dithiolan-2-ylidene)acetamido]-2,2-dimethylpenam-3-carboxylate (485 mg, 1 mmol) was dissolved in a mixture of dimethylformamide (2 mL), ethyl acetate (2 mL) and 0.5N sodium 2-ethylhexanoate/ethyl acetate solution (4 mL), and treated with triphenyl-phosphine (30 mg) and tetrakis(triphenylphosphine)palladium(0) (30 mg). The reaction mixture was stirred at room temperature for 1 h under a nitrogen atmosphere. The resulting precipitate was collected by filtration, washed successively with ethyl acetate and diethyl ether, and dried under vacuum to give the title compound (388 mg, 87%) as a light yellow powder: 1H NMR (D2O) δ 1.31 and 1.36 (each 3H, s, C2 -(CH3)2), 3.30-3.50 (4H, m, SCH2CH2S), 3.96 (1H, s, C3 -H), 5.98 (1H, d, J=5Hz, C6 -H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed successively with ethyl acetate and diethyl ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a3fd899701524795a3e706019b3bf5f3
Source dataset
uspto-grants-1995_11
Patent number
US05464616

Reaction notes

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