Hydrochloric Acid → 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid hydrochloride

HRID 1154133Notes

Reaction equation

HRID 1154133 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][C:48]([CH3:51])([CH3:50])[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:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:25]=[N:24][N:23]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.[ClH:52]>CO>[ClH:52].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:42][O:43][CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[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:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[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 1317127827-[2-(2-formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317127837-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid hydrochlorideYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-[2-(2-formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 3.5 g.) and conc. hydrochloric acid (1.9 g.) in methanol (35 ml.) was stirred at room temperature for 1.5 hours. After concentration, the residue was pulverized with diethyl ether to give 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer, 3.32 g.).

Workup

  1. concentrationAfter concentration

Sources & evidence

ORD record
ord-c880de527074445f8dba61dbea7ea31f
Source dataset
uspto-grants-1984_12
Patent number
US04487767

Reaction notes

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