Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-aminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid dihydrochloride

HRID 27278Notes

Reaction equation

HRID 27278 reaction equation
[ClH:1].C([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:42][O:43][CH3:44])[C:11]([NH:13][CH:14]2[C:40](=[O:41])[N:16]3[C:17]([C:37]([OH:39])=[O:38])=[C:18]([CH2:21][S:22][C:23]4[S:24][C:25]([CH2:28][NH:29]C(OC(C)(C)C)=O)=[N:26][N:27]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1)=O>CO>[ClH:1].[ClH:1].[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:42][O:43][CH3:44])[C:11]([NH:13][CH:14]2[C:40](=[O:41])[N:16]3[C:17]([C:37]([OH:39])=[O:38])=[C:18]([CH2:21][S:22][C:23]4[S:24][C:25]([CH2:28][NH2:29])=[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 1317118737-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 1317118747-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-aminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid dihydrochlorideYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc.hydrochloric acid (1.82 g) was added to a suspension of 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 3.9 g) in methanol (60 ml), and the mixture was stirred at room temperature for 2 hrs. After evaporation of the solvent under reduced pressure, methanol was added to the residue and evaporated again. The residue was washed with diethyl ether and dried to give 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-aminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid dihydrochloride (syn isomer, 3.0 g).

Workup

  1. customAfter evaporation of the solvent under reduced pressure, methanol
  2. additionwas added to the residue
  3. customevaporated again
  4. washThe residue was washed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-ee2b866a3bce43b79e47a1b291adb086
Source dataset
uspto-grants-1980_09
Patent number
US04220761

Reaction notes

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