Hydrochloric Acid → 7-[2-(2-Amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid hydrochloride

HRID 256431Notes

Reaction equation

HRID 256431 reaction equation
[ClH:1].C([NH:4][C:5]1[S:6][C:7]([Br:37])=[C:8]([C:10](=[N:34][O:35][CH3:36])[C:11]([NH:13][CH:14]2[C:32](=[O:33])[N:16]3[C:17]([C:29]([OH:31])=[O:30])=[C:18]([CH2:21][S:22][C:23]4[S:24][C:25]([CH3:28])=[N:26][N:27]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1)=O>CO>[ClH:1].[NH2:4][C:5]1[S:6][C:7]([Br:37])=[C:8]([C:10](=[N:34][O:35][CH3:36])[C:11]([NH:13][CH:14]2[C:32](=[O:33])[N:16]3[C:17]([C:29]([OH:31])=[O:30])=[C:18]([CH2:21][S:22][C:23]4[S:24][C:25]([CH3:28])=[N:26][N:27]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317153357-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 1317153367-[2-(2-Amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. hydrochloric acid (1.5 ml.) was added to a solution of 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer), (1.2 g.) in methanol (30 ml.) and stirred at room temperature for 7 hrs. The reaction mixture was evaporated in vacuo. To the residue was added ethyl acetate and water was removed by evaporation. The residue was pulverized with ethyl acetate and the precipitates were collected by filtration, washed with ethyl acetate and diethyl ether successively and then dried to give 7-[2-(2-amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid hydrochloride (syn isomer, 1.0 g.).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added ethyl acetate and water
  3. customwas removed by evaporation
  4. filtrationthe precipitates were collected by filtration
  5. washwashed with ethyl acetate and diethyl ether successively
  6. customdried

Sources & evidence

ORD record
ord-ccdb2a9777a44c01be77f8129e141b3a
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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