Phosphate → 7-amino-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 2412786Notes

Reaction equation

HRID 2412786 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.P([O-])([O-])([O-])=O.P([O-])([O-])(O)=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[CH2:37]([N:43]1[C:47]([SH:48])=[N:46][N:45]=[N:44]1)[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:48][C:47]3[N:43]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[N:44]=[N:45][N:46]=3)[CH2:15][S:14][C@H:9]12

Participants

7

Reactant 5

HCID 1061PhosphateHCID 10340Sodium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 4413287-Aminocephalosporanic acidHCID 178444732HCID 178444732, compound

Product 1

HCID 704323317-amino-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7-aminocephalosporanic acid (150.0 g.) was added 0.2M phosphate buffer solution (3 l.) which was prepared by dissolving sodium biphosphate dihydrate (62.1 g.) and disodium hydrogen phosphate (25.5 g.) in water (3 l.), and the resulting mixture was adjusted to pH 6.5 with 2N aqueous solution of sodium carbonate. To the mixture was added 1-hexyl-1H-tetrazole-5-thiol (154.6 g.) and the resulting mixture was stirred for 2 hours at 60° to 65° C. and at pH 6.0 to 6.5 with bubbling of nitrogen gas. The reaction mixture was adjusted to pH 3.5 with conc. hydrochloric acid under ice-cooling. Precipitates were collected by filtration and washed with water, and methanol (4 l.) and conc. hydrochloric acid (400 ml.) were added thereto. The mixture was stirred for 2 hours and an insoluble material was filtered off. The filtrate was treated with an activated charcoal and adjusted to pH 3.5 with 28 % aqueous solution of ammonia. Precipitates were collected by filtration, in turn washed with water, acetone and diethyl ether and dried to give powder of 7-amino-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (116.38 g.).

Workup

  1. customwas prepared
  2. customwith bubbling of nitrogen gas
  3. temperaturecooling
  4. customPrecipitates
  5. filtrationwere collected by filtration
  6. washwashed with water, and methanol (4 l.) and conc. hydrochloric acid (400 ml.)
  7. additionwere added
  8. stirringThe mixture was stirred for 2 hours
  9. filtrationan insoluble material was filtered off
  10. additionThe filtrate was treated with an activated charcoal
  11. customPrecipitates
  12. filtrationwere collected by filtration, in turn
  13. washwashed with water, acetone and diethyl ether
  14. customdried

Sources & evidence

ORD record
ord-59523f9dd5b24e7482e54f90db1b2d9f
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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