7-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid → HCID 131712946, compound

HRID 1164571Notes

Reaction equation

HRID 1164571 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23]OC)[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1>C(O)=O.[Zn]>[CH:18]([OH:20])=[O:19].[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[NH2:23])[N:6]=1

Participants

4

Reactant 1

HCID 1317124447-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 131712946HCID 131712946, compoundYield 184.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

Zinc powder (4.5 g) was added to a stirred solution of 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer: 3 g) in 90% formic acid (150 ml) under ice-cooling over 5 minutes, and stirred at the same temperature for 15 minutes. After the resultant solution was filtered and washed with formic acid, the filtrate and the washings were combined and concentrated under reduced pressure to a volume of about 20 ml. The concentrate was dissolved in water (150 ml) and bubbled with hydrogen sulfide gas for 20 minutes under ice-cooling. The precipitating zinc sulfide was filtered off, and the filtrate was treated with activated charcoal and lyophilized to give 7-[2-(2-amino-4-thiazolyl)glycinamido]-3-cephem-4-carboxylic acid formate (2.9 g), pale yellow powder, mp>240° C.

Workup

  1. temperaturecooling over 5 minutes
  2. filtrationAfter the resultant solution was filtered
  3. washwashed with formic acid
  4. concentrationconcentrated under reduced pressure to a volume of about 20 ml
  5. dissolutionThe concentrate was dissolved in water (150 ml)
  6. custombubbled with hydrogen sulfide gas for 20 minutes under ice-
  7. temperaturecooling
  8. filtrationThe precipitating zinc sulfide was filtered off
  9. additionthe filtrate was treated with activated charcoal

Sources & evidence

ORD record
ord-41fd9f71c46c403e8a71cd744aeec9a9
Source dataset
uspto-grants-1983_01
Patent number
US04370326

Reaction notes

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