Dimethylformamide → 7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

HRID 1154135Notes

Reaction equation

HRID 1154135 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([OH:12])=O)[N:8]=1)=[O:2].CN(C)C=O.P(Cl)(Cl)(Cl)=O.[NH2:31][CH:32]1[C:59](=[O:60])[N:34]2[C:35]([C:56]([OH:58])=[O:57])=[C:36]([CH2:39][S:40][C:41]3[N:45]([CH2:46][CH2:47][NH:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[N:44]=[N:43][N:42]=3)[CH2:37][S:38][C@H:33]12>CC(C)=O.O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([NH:31][CH:32]2[C:59](=[O:60])[N:34]3[C:35]([C:56]([OH:58])=[O:57])=[C:36]([CH2:39][S:40][C:41]4[N:45]([CH2:46][CH2:47][NH:48][C:49]([O:51][C:52]([CH3:54])([CH3:55])[CH3:53])=[O:50])[N:44]=[N:43][N:42]=4)[CH2:37][S:38][C@H:33]23)=[O:12])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 544193372-Ethoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acidHCID 704530537-amino-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317140537-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acidYield 85.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetic acid (syn isomer, 1.32 g.), N,N-dimethylformamide (447 mg.), phosphoryl chloride (939 mg.), 7-amino-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (3.0 g.), tetrahydrofuran (13 ml.) and 50% aqueous acetone (30 ml.) were treated in a similar manner to that of Example 11-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 2.78 g.).

Sources & evidence

ORD record
ord-0cdcf7ef6d014d9385cdde68ec39de6e
Source dataset
uspto-grants-1984_12
Patent number
US04487767

Reaction notes

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