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

HRID 256449Notes

Reaction equation

HRID 256449 reaction equation
[NH2:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[CH:6][CH:7]([CH3:9])[S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.P(Cl)(Cl)(Cl)=O.[CH:28]([NH:30][C:31]1[S:32][C:33]([Br:43])=[C:34]([C:36](=[N:40][O:41][CH3:42])[C:37](O)=[O:38])[N:35]=1)=[O:29]>C(OCC)(=O)C.CN(C)C=O>[CH:28]([NH:30][C:31]1[S:32][C:33]([Br:43])=[C:34]([C:36](=[N:40][O:41][CH3:42])[C:37]([NH:1][CH:2]2[C:13](=[O:14])[N:4]3[C:5]([C:10]([OH:12])=[O:11])=[CH:6][CH:7]([CH3:9])[S:8][C@H:3]23)=[O:38])[N:35]=1)=[O:29]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128022512-Methyl-7-amino-3-cephem-4-carboxylic acidHCID 538011022-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid

Product 1

HCID 1317153637-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methyl-3-cephem-4-carboxylic acidYield 78.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7-amino-2-methyl-3-cephem-4-carboxylic acid (1.0 g.) and trimethylsilylacetamide (3.7 g.) in dry ethyl acetate (30 ml.) and a solution of dimethylformamide (0.47 ml.), phosphoryl chloride (0.56 ml.) and 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 1.6 g.) in dry ethyl acetate (11.6 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]-2-methyl-3-cephem-4-carboxylic acid (syn isomer, 1.85 g.).

Sources & evidence

ORD record
ord-56d58639de7547378db8a1ca70e36e4d
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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