Phosphorus oxychloride → 7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-benzoyloxymethyl-3-cephem-4-carboxylic acid

HRID 568852Notes

Reaction equation

HRID 568852 reaction equation
[NH2:1][CH:2]1[C:22](=[O:23])[N:4]2[C:5]([C:19]([OH:21])=[O:20])=[C:6]([CH2:9][O:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.P(Cl)(Cl)(Cl)=O.[CH:37]([NH:39][C:40]1[S:41][C:42]([Br:52])=[C:43]([C:45](=[N:49][O:50][CH3:51])[C:46](O)=[O:47])[N:44]=1)=[O:38]>C(OCC)(=O)C.CN(C)C=O>[CH:37]([NH:39][C:40]1[S:41][C:42]([Br:52])=[C:43]([C:45](=[N:49][O:50][CH3:51])[C:46]([NH:1][CH:2]2[C:22](=[O:23])[N:4]3[C:5]([C:19]([OH:21])=[O:20])=[C:6]([CH2:9][O:10][C:11](=[O:18])[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:7][S:8][C@H:3]23)=[O:47])[N:44]=1)=[O:38]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 538011022-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acidHCID 704174247-Amino-3-benzoyloxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317153567-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-benzoyloxymethyl-3-cephem-4-carboxylic acidYield 34.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7-amino-3-benzoyloxymethyl-3-cephem-4-carboxylic acid (0.67 g.) and trimethylsilylacetamide (2.1 g.) in dry ethyl acetate (20 ml.) and a solution of dimethylformamide (0.2 ml.), phosphoryl chloride (0.24 ml.) and 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 0.62 g.) in dry ethyl acetate (1 ml.) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-benzoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 430 mg.).

Sources & evidence

ORD record
ord-01d228beb4ee43b0a9129b9d21c29408
Source dataset
uspto-grants-1988_03
Patent number
US04729991

Reaction notes

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