Triphenylphosphine → HCID 86749086, compound

HRID 128501Notes

Reaction equation

HRID 128501 reaction equation
[S:1]1[CH2:5][CH2:4][S:3][C:2]1=[C:6]([C:26]([O:28][CH3:29])=[O:27])[C:7]([NH:9][C@@H:10]1[C:24](=[O:25])[N:12]2[CH:13]([C:18]([O:20]CC=C)=[O:19])[C:14]([CH3:17])([CH3:16])[S:15][C@H:11]12)=[O:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+:59].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>[S:3]1[CH2:4][CH2:5][S:1][C:2]1=[C:6]([C:26]([O:28][CH3:29])=[O:27])[C:7]([NH:9][C@@H:10]1[C:24](=[O:25])[N:12]2[CH:13]([C:18]([O-:20])=[O:19])[C:14]([CH3:17])([CH3:16])[S:15][C@H:11]12)=[O:8].[Na+:59]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 15297251HCID 15297251, compoundHCID 86749088HCID 86749088, compound

Product 1

HCID 86749086HCID 86749086, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Allyl 6β-[(1,3-dithiolan-2-ylidene)(methoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate (459 mg, 1 mmol) was dissolved in 0.25N sodium 2-ethylhexanoate/ethyl acetate solution (4 mL), and treated with triphenylphosphine (30 mg) and tetrakis(triphenylphosphine)palladium(0) (30 mg). The reaction mixture was stirred at room temperature for 2 h under a nitrogen atmosphere. The resulting precipitate was collected by filtration, washed with ethyl acetate and diethyl ether, and dried in vacuo to yield the title compound (368 mg, 84%) as a light yellow powder: 1H NMR (D2O) δ 1.40 and 1.50 (each 3H, s, C2 -(CH3)2), 3.25-3.45 (4H, m, SCH2CH2S), 3.69 (3H, s, OCH3), 4.13 (1H, s, C3 -H), 5.45-5.52 (2H, m, C5 -H and C6).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with ethyl acetate and diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-677d17838aaf4f04bd3bc86545bcc9c0
Source dataset
uspto-grants-1995_11
Patent number
US05464616

Reaction notes

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