Hydrochloric Acid → HCID 70503890, compound

HRID 1979790Notes

Reaction equation

HRID 1979790 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:21])[CH2:19][Cl:20])[C:15](=[O:22])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.C(=O)([O-])O.[Na+].[Cl-].[Ca+2].[Cl-].Cl>CO>[Cl:20][CH2:19][C:18]([NH:17][CH:16]1[C:15](=[O:22])[N:10]2[C:11]([C:12]([OH:14])=[O:13])=[C:6]([CH2:5][O:4][CH3:1])[CH2:7][S:8][C@H:9]12)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5284359Calcium ChlorideHCID 70504102HCID 70504102, compound

Product 1

HCID 70503890HCID 70503890, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

2 g of 3-acetoxymethyl-7-chloroacetamido-3-cephem-4-carboxylic acid and 483 mg of sodium hydrogen carbonate were dissolved in 20 ml of 60% v/v aqueous methanol, and 30 g of anhydrous calcium chloride were added. The mixture was then stirred at 70° C. for 50 minutes, after which it was diluted with 50 ml of ice-water, its pH was adjusted to a value of 1-2 by the addition of hydrochloric acid, and it was extracted three times, each time with 50 ml of ethyl acetate. The ethyl acetate extracts were combined, washed with an aqueous solution of sodium chloride, dehydrated over anhydrous magnesium sulphate and concentrated by evaporation under reduced pressure to give 1.3 g of 7-chloroacetamido-3-methoxymethyl-3-cephem-4-carboxylic acid in an impure state as an amorphous solid.

Workup

  1. additionwere added
  2. extractionwas extracted three times
  3. washwashed with an aqueous solution of sodium chloride
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fcf8bcfe30b44f198d99478afe3279b1
Source dataset
uspto-grants-1984_11
Patent number
US04482710

Reaction notes

Loading…