Sodium borohydride → HCID 88737033, compound

HRID 1164572Notes

Reaction equation

HRID 1164572 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:23])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[BH4-].[Na+]>CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:7]([OH:23])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 88656749HCID 88656749, compound

Product 1

HCID 88737033HCID 88737033, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 7-[2-(2-amino-4-thiazolyl)glyoxyloylamino]-3-cephem-4-carboxylic acid (520 mg) in methanol (15 ml) was added sodium borohydride (100 mg) under ice-cooling, and stirred at the same temperature for 3 hours. Methanol was distilled off under reduced pressure from the reaction mixture, and the residue was dissolved in water (3 ml) and adjusted to pH 3 with 6 N-hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide to give 7-[2-(2-amino-4-thiazolyl)-2-hydroxyacetamido]-3-cephem-4-carboxylic acid (290 mg).

Workup

  1. temperaturecooling
  2. distillationMethanol was distilled off under reduced pressure from the reaction mixture
  3. dissolutionthe residue was dissolved in water (3 ml)
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-a0f2addcae7b41579f7b470823bd1838
Source dataset
uspto-grants-1983_01
Patent number
US04370326

Reaction notes

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