Phosphorus trichloride → HCID 70505024, compound

HRID 1463143Notes

Reaction equation

P(Cl)(Cl)Cl.[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]([NH:13][CH:14]1[C:44](=[O:45])[N:16]2[C:17]([C:28]([O:30][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])=[C:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[CH:19]([CH3:22])[S:20](=O)[C@H:15]12)=[O:12]>CN(C=O)C>[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]([NH:13][CH:14]1[C:44](=[O:45])[N:16]2[C:17]([C:28]([O:30][CH:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[O:29])=[C:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@H:19]([CH3:22])[S:20][C@H:15]12)=[O:12]

Participants

Conditions

Temperature: -30 °C

Procedure

A 41.5 ml portion of PCl3 was added to a solution of 32 g of diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-acetoxymethylceph-3-em-4-carboxylate 1-oxide in 200 ml of DMF at -50° C., and the mixture was stirred at -30° C. for 5 minutes and poured in ice water to extract with AcOEt. The AcOEt layer was washed with 5% aqueous NaHCO3 and saturated aqueous sodium chloride solutions, and dried over Na2SO4, followed by distilling off the AcOET under reduced pressure, thus yielding crude crystals. Recrystalization from AcOEt-Et2O (1:3) afforded 17 g (55%) of diphenylmethyl 7-(2-thienylacetamido)-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylate.

Workup

extractionto extract with AcOEt
washThe AcOEt layer was washed with 5% aqueous NaHCO3 and saturated aqueous sodium chloride solutions
dry with materialdried over Na2SO4
distillationby distilling off the AcOET under reduced pressure
customthus yielding crude crystals
customRecrystalization from AcOEt-Et2O (1:3)

Sources & evidence

ORD record: ord-a8ae9072ccea4b5fa7f7945509cf2e2f
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04463172

Reaction notes

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