Hydrochloric Acid → HCID 131712326, compound

HRID 1758415Notes

Reaction equation

HRID 1758415 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][CH2:28][NH:29]C(OC(C)(C)C)=O)[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.[ClH:37]>CO>[ClH:37].[ClH:37].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][CH2:28][NH2:29])[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 131712325HCID 131712325, compound

Product 1

HCID 131712326HCID 131712326, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]3-cephem-4-carboxylic acid (syn isomer, 0.70 g.), conc. hydrochloric acid (0.48 g.) and methanol (7 ml.) was stirred at room temperature for 4 hours. After concentrating the resultant solution in vacuo, the residue was dissolved in methanol (10 ml.) and crystallized by adding diisopropyl ether (20 ml.). The precipitates were collected by filtration, washed with a mixture of methanol and diisopropyl ether (1:1) and dried to give 7-[2-(2-aminothiazol-4-yl)-2-(2-aminoethoxyimino)acetamido]-3-cephem-4-carboxylic acid dihydrochloride (syn isomer, 0.58 g.).

Workup

  1. concentrationAfter concentrating the resultant solution in vacuo
  2. dissolutionthe residue was dissolved in methanol (10 ml.)
  3. customcrystallized
  4. additionby adding diisopropyl ether (20 ml.)
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with a mixture of methanol and diisopropyl ether (1:1)
  7. customdried

Sources & evidence

ORD record
ord-a4f40d8fb4cb43e0aebec78b1b3f8faa
Source dataset
uspto-grants-1983_02
Patent number
US04372952

Reaction notes

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