Water → Benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate

HRID 980984Notes

Reaction equation

HRID 980984 reaction equation
P(Cl)(Cl)Cl.[C:5]1([CH2:11][C:12]([NH:14][CH:15]2[C:47](=[O:48])[N:17]3[C:18]([C:31]([O:33][CH:34]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:32])=[C:19]([CH:23]=[CH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:20][S:21](=O)[C@H:16]23)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CN(C)C=O>[C:5]1([CH2:11][C:12]([NH:14][CH:15]2[C:47](=[O:48])[N:17]3[C:18]([C:31]([O:33][CH:34]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[C:19]([CH:23]=[CH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:20][S:21][C@H:16]23)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24387Phosphorus trichlorideHCID 131714361Benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 131714363Benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylateYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus trichloride (15.2 g) was added to the solution of benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate-1-oxide (trans isomer) (22.2 g) in dimethylformamide (220 ml) at -30° C. and the solution was stirred at -30° to -25° C. for 10 minutes. The reaction mixture was poured into cold water (1 l) and resulting precipitates were collected by filtration. The filtrate was dissolved in ethyl acetate (300 ml) and the ethyl acetate layer was washed with brine, dried over magnesium sulfate and evaporated to give benzhydryl 7-phenylacetamido-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate (trans isomer) (15.9 g).

Workup

  1. customresulting
  2. customprecipitates
  3. filtrationwere collected by filtration
  4. dissolutionThe filtrate was dissolved in ethyl acetate (300 ml)
  5. washthe ethyl acetate layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-4d9bc0a374904ddfa03612008ecbceaa
Source dataset
uspto-grants-1987_01
Patent number
US04639448

Reaction notes

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