Hydrochloric Acid → 7-[2-(2-aminothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-[1-(2-aminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

HRID 1154136Notes

Reaction equation

HRID 1154136 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:42][O:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:10]([NH:12][CH:13]2[C:40](=[O:41])[N:15]3[C:16]([C:37]([OH:39])=[O:38])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH2:27][CH2:28][NH:29]C(OC(C)(C)C)=O)[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>C(O)C>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:42][O:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:10]([NH:12][CH:13]2[C:40](=[O:41])[N:15]3[C:16]([C:37]([OH:39])=[O:38])=[C:17]([CH2:20][S:21][C:22]4[N:26]([CH2:27][CH2:28][NH2:29])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317140537-[2-(2-formamidothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317140547-[2-(2-aminothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-[1-(2-aminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acidYield 25.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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, 2.7 g.), conc. hydrochloric acid (1.52 g.) and ethanol (27 ml.) were treated in a similar manner to that of Example 11-(2) to give 7-[2-(2-aminothiazol-4-yl)-2-ethoxycarbonylmethoxyiminoacetamido]-3-[1-(2-aminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 0.57 g.).

Sources & evidence

ORD record
ord-2aed11c83f3c49c7803734cf32f4df86
Source dataset
uspto-grants-1984_12
Patent number
US04487767

Reaction notes

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