Hydrochloric Acid → HCID 178460192, compound

HRID 1982668Notes

Reaction equation

HRID 1982668 reaction equation
Cl.C([NH:4][C:5]1[N:10]=[C:9]([C:11](=[N:35][O:36][CH2:37][C:38]#[CH:39])[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])[CH:8]=[CH:7][CH:6]=1)=O>CO>[NH2:4][C:5]1[N:10]=[C:9]([C:11](=[N:35][O:36][CH2:37][C:38]#[CH:39])[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])[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178460190HCID 178460190, compound

Product 1

HCID 178460192HCID 178460192, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. Hydrochloric acid (0.43 ml.) was added to a solution of 7-[2-(6-formamidopyridin-2-yl)-2-propargyloxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (2.35 g.) in methanol (15 ml.), and the mixture was stirred at ambient temperature for 30 minutes. The methanol was removed by distillation under reduced pressure from the reaction mixture, and the remaining aqueous solution was diluted with water (100 ml.) and then adjusted to pH 2 with an aqueous solution of sodium bicarbonate. The precipitating crystals were collected by filtration, washed with water and then dried to give 7-[2-(6-aminopyridin-2-yl)-2-propargyloxyiminoacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (1.05 g.), m.p. 163°-165° C. (dec.).

Workup

  1. customThe methanol was removed by distillation under reduced pressure from the reaction mixture
  2. additionthe remaining aqueous solution was diluted with water (100 ml.)
  3. filtrationThe precipitating crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-78de01e2048e45c3a74254521093e91d
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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