Water → Benzhydryl 7-tert-butoxycarbonylamino-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate

HRID 1380965Notes

Reaction equation

HRID 1380965 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:42](=[O:43])[N:11]2[C:12]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:13]([CH:17]=[CH:18][S:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH2:14][S:15](=O)[C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)Cl.C(OCC)(=O)C.O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:42](=[O:43])[N:11]2[C:12]([C:26]([O:28][CH:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:27])=[C:13]([CH:17]=[CH:18][S:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24387Phosphorus trichlorideHCID 131714627HCID 131714627, compound

Product 1

HCID 131714629Benzhydryl 7-tert-butoxycarbonylamino-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylateYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzhydryl 7-tert-butoxycarbonylamino-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate-1-oxide (trans isomer) (12.3 g) in dimethylformamide (70 ml) was added phosphorus trichloride (5.5 g) at -40° C. After being stirred at the same temperature for 30 minutes, the reaction mixture was poured into a mixture of ethyl acetate (200 ml) and water (100 ml). The separated organic layer was washed in turn with 5% aqueous sodium bicarbonate, water, and brine. The solvent was evaporated in vacuo to give benzhydryl 7-tert-butoxycarbonylamino-3-[2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate (trans isomer) (11.1 g).

Workup

  1. washThe separated organic layer was washed in turn with 5% aqueous sodium bicarbonate, water, and brine
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-610d88253eef4f39bfc77708d85b1221
Source dataset
uspto-grants-1986_04
Patent number
US04584290

Reaction notes

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