Hydrochloric Acid → 7-Amino-3-azidomethyl-3-cephem-4-carboxylic acid

HRID 2118582Notes

Reaction equation

HRID 2118582 reaction equation
C(O[CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH2:17])[C:15](=[O:18])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.[N-:19]=[N+:20]=[N-:21].[Na+].C(=O)(O)[O-].[Na+].Cl>P([O-])([O-])([O-])=O>[NH2:17][CH:16]1[C:15](=[O:18])[N:10]2[C:11]([C:12]([OH:14])=[O:13])=[C:6]([CH2:5][N:19]=[N+:20]=[N-:21])[CH2:7][S:8][C@H:9]12

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 33557Sodium AzideHCID 516892Sodium Bicarbonate2×HCID 113463103-Acetoxymethyl-7-amino-3cephem-4-carboxylic acid

Product 1

HCID 128022197-Amino-3-azidomethyl-3-cephem-4-carboxylic acidYield 40%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

To a stirred suspension of 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid (45.3 g.) in a phosphate buffer (pH 6.4; 700 ml.) was added sodium azide (10.8 g.), then in small portions sodium bicarbonate (14 g.). The stirred mixture was then immersed in a 60° bath for 6 hours, the pH being maintained at 6.4 by addition of 2N aqueous HCl or 5% w/v aqueous sodium bicarbonate solutions. After cooling the pH of the mixture was adjusted to 3-3.5 with 2N aqueous HCl. The resulting precipitate was separated, washed with water and acetone then dried over P2O5 to give 7-amino-3-azidomethylceph-3-em-4-carboxylic acid (40%).

Workup

  1. customwas then immersed in a 60°
  2. customfor 6 hours
  3. temperatureAfter cooling the pH of the mixture
  4. customThe resulting precipitate was separated
  5. washwashed with water and acetone
  6. dry with materialthen dried over P2O5

Sources & evidence

ORD record
ord-7c1ba276e5974a198ec2fbb46c78e293
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

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