Hydrochloric Acid → 7-Amino-3-methylenecepham-4-carboxylic acid

HRID 463410Notes

Reaction equation

HRID 463410 reaction equation
CC(O[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.Cl.[OH-].[Na+]>O.[Zn]>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[CH:7]([C:16]([OH:18])=[O:17])[C:6](=[CH2:5])[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 130225477-Amino-3-methylenecepham-4-carboxylic acidYield 55.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

Zinc powder (40 g) was added to a solution of 7-aminocephalosporanic acid (27.3 g) and conc. hydrochloric acid (70 ml.) in water (200 ml.) for 5° C. and stirred for an hour. The resultant solution was adjusted to pH 4.0 with 4N sodium hydroxide and concentrated to 100 ml. of the volume. After adjusting the solution to pH 4.0, the solution was allowed to stand under cooling overnight. The precipitates were collected by filtration to give 7-amino-3-methylenecepham-4-carboxylic acid (11.96 g.).

Workup

  1. concentrationconcentrated to 100 ml
  2. temperatureunder cooling overnight
  3. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-b42a2c818369442692913e7afb898be2
Source dataset
uspto-grants-1985_05
Patent number
US04518774

Reaction notes

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