Hydrochloric Acid → 7alpha-Chloro-3-methyl-3-cephem-4-carboxylic acid

HRID 258010Notes

Reaction equation

HRID 258010 reaction equation
[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H:6](N)[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13].C(O)C.[ClH:18].N([O-])=O.[Na+]>[Cl-].[Na+].O.O>[Cl:18][C@H:6]1[C:7](=[O:8])[N:4]2[C:3]([C:12]([OH:14])=[O:13])=[C:2]([CH3:1])[CH2:11][S:10][C@H:5]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 334987-Aminodeacetoxycephalosporanic acidHCID 23668193Sodium Nitrite

Product 1

HCID 156604937alpha-Chloro-3-methyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 7-ADCA (25 g, 0.117 mol), ethanol (700 ml), water (163 ml) and concentrated hydrochloric acid (163 ml) was cooled to 5° C. Sodium nitrite (11.5 g, 0.167 mol) was added in small portions over 25 minutes and the mixture was stirred for 3.5 hours at 0° C.-5° C.; 300 ml of brine was added and the reaction mixture was extracted with methylene chloride. The organic extract was washed with water, brine, dried over sodium sulfate and concentrated (16.1 g, 58.9%). This crude acid was directly used for the next step without further purification.

Workup

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated (16.1 g, 58.9%)
  6. customThis crude acid was directly used for the next step without further purification

Sources & evidence

ORD record
ord-dd6075fc0030475e83791d0bbd7aea26
Source dataset
uspto-grants-1993_11
Patent number
US05264429

Reaction notes

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