Hydrochloric Acid → HCID 131712324, compound

HRID 1758413Notes

Reaction equation

HRID 1758413 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH3:31])[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][CH2:28][O:29][CH2:30][CH3:31])[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 131712323HCID 131712323, compound

Product 1

HCID 131712324HCID 131712324, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.2 g.), conc hydrochloric acid (2 ml.) and methanol (30 ml.) was stirred at room temperature for 1.6 hours. After concentrating the resultant solution in vacuo, water was added to the residue, adjusted to pH 6.5 with sodium bicarbonate and washed with ethyl acetate. The aqueous solution was treated with activated charcoal and adjusted to pH 3.0 with conc. hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-(2-aminothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.87 g.).

Workup

  1. concentrationAfter concentrating the resultant solution in vacuo, water
  2. additionwas added to the residue
  3. washwashed with ethyl acetate
  4. additionThe aqueous solution was treated with activated charcoal
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-e3ea5c0f94c2485cb7b8fa94c1aaa7a6
Source dataset
uspto-grants-1983_02
Patent number
US04372952

Reaction notes

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