Hydrochloric Acid → (6R-trans)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

HRID 1762425Notes

Reaction equation

HRID 1762425 reaction equation
CC([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[OH-].[Na+].Cl>O>[NH2:13][C@@H:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][OH:4])[CH2:15][S:14][C@H:9]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4413287-Aminocephalosporanic acid3×

Product 1

HCID 11031679(6R-trans)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidYield 63.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 100 ml of water was suspended 10 g of 7-aminocephalosporanic acid (hereinafter abbreviated as "7-ACA"), to which was added gradually, while stirring under ice-cooling, a 2N aqueous solution of sodium hydroxide to keep the pH in a range from 12.5 to 13.4. The mixture was stirred for about 2 hours, which was then subjected to TLC. When disappearance of 7-ACA was confirmed, the pH was adjusted to 3.4 by the addition of 4N HCl. Precipitating crystals were collected by filtration, washed with water and acetone, followed by drying over phosphorus pentachloride under reduced pressure to give 5.4 g of 7β-amino-3-hydroxymethyl-3-cephem-4-carboxylic acid as pale yellow crystals.

Workup

  1. additionwas added gradually
  2. temperaturecooling
  3. stirringThe mixture was stirred for about 2 hours
  4. customPrecipitating crystals
  5. filtrationwere collected by filtration
  6. washwashed with water and acetone
  7. dry with materialby drying over phosphorus pentachloride under reduced pressure

Sources & evidence

ORD record
ord-8a91d1638532438fa05cf6cd3a67c9ad
Source dataset
uspto-grants-1989_05
Patent number
US04833134

Reaction notes

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