Hydrochloric Acid → HCID 178460193, compound

HRID 2286639Notes

Reaction equation

HRID 2286639 reaction equation
Cl.[CH2:2]([O:5][N:6]=[C:7]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH:37]C=O)[N:32]=1)[C:8]([NH:10][CH:11]1[C:29](=[O:30])[N:13]2[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH:18]([S:20][C:21]3[NH:25][N:24]=[N:23][N:22]=3)[CH3:19])[CH2:16][S:17][C@H:12]12)=[O:9])[CH:3]=[CH2:4]>CO>[CH2:2]([O:5][N:6]=[C:7]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[N:32]=1)[C:8]([NH:10][CH:11]1[C:29](=[O:30])[N:13]2[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH:18]([S:20][C:21]3[NH:25][N:24]=[N:23][N:22]=3)[CH3:19])[CH2:16][S:17][C@H:12]12)=[O:9])[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178460191HCID 178460191, compound

Product 1

HCID 178460193HCID 178460193, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. hydrochloric acid (0.31 ml.) was added to a solution of 7-[2-allyloxyimino-2-(6-formamidopyridin-2-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (1.75 g.) in methanol (7 ml.), and the mixture was stirred at ambient temperature for 30 minutes. The methanol was removed by distillation from the reaction mixture, and the remaining aqueous solution was diluted with water (80 ml.) and then adjusted to pH 2-3 with an aqueous solution of sodium bicarbonate. The aqueous solution was subjected to column chromatography on a macroporous, non-ionic adsorption resin "Diaion HP-20" (Trade Mark, manufactured by Mitsubishi Chemical Industries Ltd.) (50 ml.). After the column was washed with water (1 l.), elution was carried out with 50% aqueous methanol (1 l.) and fractions containing the desired compound were collected. The methanol was removed by distillation from the combined fractions under reduced pressure and the resultant aqueous solution was lyophilized to give 7-[2-allyloxyimino-2-(6-aminopyridin-2-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (1.13 g.), mp. 149°-151° C. (dec.).

Workup

  1. customThe methanol was removed by distillation from the reaction mixture
  2. additionthe remaining aqueous solution was diluted with water (80 ml.)
  3. washAfter the column was washed with water (1 l.), elution
  4. additioncontaining the desired compound
  5. customwere collected
  6. customThe methanol was removed by distillation from the combined fractions under reduced pressure

Sources & evidence

ORD record
ord-5deb03df26234958ab43efe90219264e
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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