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Phosphorus oxychloride → 7-[2-(2-Formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

HRID 568850
Notes
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Reaction equation

HRID 568850 reaction equation
[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[S:12][CH:13]=[N:14][N:15]=3)[CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.P(Cl)(Cl)(Cl)=O.[CH:34]([NH:36][C:37]1[S:38][C:39]([Cl:49])=[C:40]([C:42](=[N:46][O:47][CH3:48])[C:43](O)=[O:44])[N:41]=1)=[O:35]>C(OCC)(=O)C.CN(C)C=O>[CH:34]([NH:36][C:37]1[S:38][C:39]([Cl:49])=[C:40]([C:42](=[N:46][O:47][CH3:48])[C:43]([NH:1][CH:2]2[C:19](=[O:20])[N:4]3[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]4[S:12][CH:13]=[N:14][N:15]=4)[CH2:7][S:8][C@H:3]23)=[O:44])[N:41]=1)=[O:35]
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 538747752-(2-Formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetic acid

Product 1

HCID 1317153537-[2-(2-Formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid
Yield 98.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7-amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acid (4.3 g.) and trimethylsilylacetamide (17.1 g.) in dry ethyl acetate (130 ml.) and a solution of dimethylformamide (0.92 ml.), phosphoryl chloride (1.09 ml.) and 2-(2-formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 2.6 g.) in dry ethyl acetate (27 ml.) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 5.6 g.).

Sources & evidence

ORD record
ord-d630dace3e9644d89aa5fcf27306ff62
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04729991

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes