Water → HCID 131714110, compound

HRID 615416Notes

Reaction equation

HRID 615416 reaction equation
P(Cl)(Cl)Cl.[C:5]([O:9][C:10]([CH2:12][O:13][N:14]=[C:15]([C:37]1[N:38]=[CH:39][S:40][CH:41]=1)[C:16]([NH:18][CH:19]1[C:35](=[O:36])[N:21]2[C:22]([C:32]([OH:34])=[O:33])=[C:23]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][S:25](=O)[C@H:20]12)=[O:17])=[O:11])([CH3:8])([CH3:7])[CH3:6].O.C(OCC)(=O)C>CN(C)C=O>[C:5]([O:9][C:10]([CH2:12][O:13][N:14]=[C:15]([C:37]1[N:38]=[CH:39][S:40][CH:41]=1)[C:16]([NH:18][CH:19]1[C:35](=[O:36])[N:21]2[C:22]([C:32]([OH:34])=[O:33])=[C:23]([CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][S:25][C@H:20]12)=[O:17])=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24387Phosphorus trichlorideHCID 131714111HCID 131714111, compound

Product 1

HCID 131714110HCID 131714110, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus trichloride (1.5 g) was added to a solution of 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-mesylmethyl-3-cephem-4-carboxylic acid-1-oxide (syn isomer (2.1 g) in N,N-dimethylformamide (20 ml) at -50° C. and the solution was stirred at -40° to -30° C. for 10 minutes. The reaction mixture was poured into a mixture of cold water (200 ml) and ethyl acetate (150 ml). The separated organic layer was washed with water (50 ml), dried over magnesium sulfate and evaporated to give 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-mesylmethyl-3-cephem-4-carboxylic acid (syn isomer) (0.9 g).

Workup

  1. washThe separated organic layer was washed with water (50 ml)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-9214de108a7f4d41a3c3fe593968f77c
Source dataset
uspto-grants-1985_02
Patent number
US04499088

Reaction notes

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