Hydrochloric Acid → HCID 178502762, compound

HRID 1982666Notes

Reaction equation

HRID 1982666 reaction equation
Cl.C([NH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11](=[N:35][O:36][CH3:37])[C:12]([NH:14][CH:15]2[C:33](=[O:34])[N:17]3[C:18]([C:30]([OH:32])=[O:31])=[C:19]([CH:22]([S:24][C:25]4[NH:29][N:28]=[N:27][N:26]=4)[CH3:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:6]=1)=O>CO>[NH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11](=[N:35][O:36][CH3:37])[C:12]([NH:14][CH:15]2[C:33](=[O:34])[N:17]3[C:18]([C:30]([OH:32])=[O:31])=[C:19]([CH:22]([S:24][C:25]4[NH:26][N:27]=[N:28][N:29]=4)[CH3:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178502761HCID 178502761, compound

Product 1

HCID 178502762HCID 178502762, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc.hydrochloric acid (0.36 ml) was added to a solution of 7-[2-(4-formamidopyrimidin-2-yl)-2-methoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (1.9 g) in methanol (38 ml), and the mixture was stirred at ambient temperature for 5.5 hours. The reaction mixture was concentrated, and the concentrate was diluted with water and then washed with ethyl acetate. After the ethyl acetate in the aqueous solution was removed by distillation, 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.) (110 ml). Elution was carried out with water (400 ml), 10% aqueous methanol (100 ml.), 20% aqueous methanol (200 ml.) and then 30% aqueous methanol (2 l.), and the fractions containing the desired compound were collected. The combined fractions were evaporated to dryness under reduced pressure to give powders (1.0 g) of 7-[2-(4-aminopyrimidin-2-yl)-2-methoxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (a mixture of syn and anti isomer), mp. 150°-160° C. (dec.).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe concentrate was diluted with water
  3. washwashed with ethyl acetate
  4. customAfter the ethyl acetate in the aqueous solution was removed by distillation
  5. washElution
  6. addition30% aqueous methanol (2 l.), and the fractions containing the desired compound
  7. customwere collected
  8. customThe combined fractions were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-86289497abec41de92056daf04f6707c
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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