Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid hydrochloride

HRID 255754Notes

Reaction equation

HRID 255754 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:30][O:31][CH2:32][CH2:33][O:34]C=O)[C:10]([NH:12][CH:13]2[C:28](=[O:29])[N:15]3[C:16]([C:25]([OH:27])=[O:26])=[C:17]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.[ClH:37].O1CCCC1>CO>[ClH:37].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:30][O:31][CH2:32][CH2:33][OH:34])[C:10]([NH:12][CH:13]2[C:28](=[O:29])[N:15]3[C:16]([C:25]([OH:27])=[O:26])=[C:17]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1317152787-[2-(2-Formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317152797-[2-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid hydrochlorideYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 1.5 g.), conc. hydrochloric acid (0.6 g.), tetrahydrofuran (7.5 ml.) and methanol (15.0 ml.) was stirred at room temperature for 6 hours. After concentrating the resultant solution in vacuo, the residue was pulverized with a mixture of methanol and diisopropyl ether. The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-[2-(2-aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer, 1.36 g.).

Workup

  1. concentrationAfter concentrating the resultant solution in vacuo
  2. additionthe residue was pulverized with a mixture of methanol and diisopropyl ether
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-807344495efa40adaad5d2cbc2edcc02
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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