Phosphorus oxychloride → 7-(2-Methoxyimino-3,3-ethylenedioxy-4-bromobutyramido)-3-cephem-4-carboxylic acid

HRID 1154823Notes

Reaction equation

HRID 1154823 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][N:8]=[C:9]([C:13]1([O:19][CH2:18][CH2:17][O:16]1)[CH2:14][Br:15])[C:10]([OH:12])=O.[NH2:20][CH:21]1[C:31](=[O:32])[N:23]2[C:24]([C:28]([OH:30])=[O:29])=[CH:25][CH2:26][S:27][C@H:22]12.C[Si](CC(N)=O)(C)C>C(OCC)(=O)C.CN(C)C=O>[CH3:6][O:7][N:8]=[C:9]([C:13]1([O:19][CH2:18][CH2:17][O:16]1)[CH2:14][Br:15])[C:10]([NH:20][CH:21]1[C:31](=[O:32])[N:23]2[C:24]([C:28]([OH:30])=[O:29])=[CH:25][CH2:26][S:27][C@H:22]12)=[O:12]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 536757272-Methoxyimino-3,3-ethylenedioxy-4-bromobutyric acid

Product 1

HCID 1317125337-(2-Methoxyimino-3,3-ethylenedioxy-4-bromobutyramido)-3-cephem-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus oxychloride (0.54 ml.), N,N-dimethylformamide (438 mg.), 2-methoxyimino-3,3-ethylenedioxy-4-bromobutyric acid (syn isomer, 1.6 g.), 7-amino-3-cephem-4-carboxylic acid (1 g.), trimethylsilylacetamide (3.3 g.) and dry ethyl acetate (21 ml.) were treated in a similar manner to that of Example 11 (1) to give 7-(2-methoxyimino-3,3-ethylenedioxy-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 2.25 g.)

Sources & evidence

ORD record
ord-7f51df03d2bc4616aa17c6cccd7897fd
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

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