Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-methylthiomethoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 745406Notes

Reaction equation

HRID 745406 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][S:28][CH3:29])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][S:28][CH3:29])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131712319HCID 131712319, compound

Product 1

HCID 1317123207-[2-(2-Aminothiazol-4-yl)-2-methylthiomethoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 48.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-methylthiomethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.22 g.), conc. hydrochloric acid (0.25 g.) and methanol (3.3 ml.) was stirred at room temperature for 2.3 hours. After concentrating the resultant solution in vacuo, the residue was poured into water, adjusted to pH 7 with 10% aqueous sodium hydroxide and washed with ethyl acetate. The aqueous solution was adjusted to pH 3 with 10% hydrochloric acid under ice cooling and stirred at the same temperature for 30 minutes. The precipitates were collected by filtration, washed with water and dried to give 7-[2-(2-aminothiazol-4-yl)-2-methylthiomethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.1 g.).

Workup

  1. concentrationAfter concentrating the resultant solution in vacuo
  2. additionthe residue was poured into water
  3. washwashed with ethyl acetate
  4. stirringstirred at the same temperature for 30 minutes
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-bae35f3b9c8c41b59b2ab189eb0cdbac
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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