Phosphorus oxychloride → 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid

HRID 256434Notes

Reaction equation

HRID 256434 reaction equation
[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]([S:11][C:12]3[NH:16][N:15]=[N:14][N:13]=3)[CH3:10])[CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.P(Cl)(Cl)(Cl)=O.[CH:35]([NH:37][C:38]1[S:39][C:40]([Br:50])=[C:41]([C:43](=[N:47][O:48][CH3:49])[C:44](O)=[O:45])[N:42]=1)=[O:36]>C(OCC)(=O)C.CN(C)C=O>[CH:35]([NH:37][C:38]1[S:39][C:40]([Br:50])=[C:41]([C:43](=[N:47][O:48][CH3:49])[C:44]([NH:1][CH:2]2[C:20](=[O:21])[N:4]3[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]([S:11][C:12]4[NH:13][N:14]=[N:15][N:16]=4)[CH3:10])[CH2:7][S:8][C@H:3]23)=[O:45])[N:42]=1)=[O:36]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 538011022-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acidHCID 1784773817-Amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 1785027637-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acidYield 41.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7-amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (660 mg.) and trimethylsilylacetamide (1.3 g.) in dry ethyl acetate (23 ml.) and a mixture of dimethylformamide (0.2 ml.), phosphoryl chloride (0.24 ml.), dry ethyl acetate (10 ml.) and 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 740 mg.) 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-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 520 mg.).

Workup

  1. additionwere treated in a similar manner to that of Example 1-(1)

Sources & evidence

ORD record
ord-152691370b2c46f2b8284599f0f82a90
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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