Methanol → 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-propanesulfonylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

HRID 325400Notes

Reaction equation

HRID 325400 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:36])[C:22]([C:24]4[N:25]=[C:26]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[S:27][CH:28]=4)=[O:23])[C:18](=[O:37])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1.CO.[OH-].[Na+].[BH4-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:36])[CH:22]([OH:23])[C:24]4[N:25]=[C:26]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[S:27][CH:28]=4)[C:18](=[O:37])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1

Participants

7

Reactant 5

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 1317125673-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-(2-propanesulfonylamino-1,3-thiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acidHCID 178461071HCID 178461071, compound

Product 1

HCID 887048183-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-propanesulfonylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-(2-propanesulfonylamino-1,3-thiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, which can be represented as 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-(2-propanesulfonylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, (8.0 g.), methanol (160 ml.) and 1 N sodium hydroxide aqueous solution (13.6 ml.) was dropwise added a mixture of sodium borohydride (0.26 g.) and ethanol (15 ml.) over 20 minutes under stirring and ice-cooling. The mixture was further stirred for 1 hour, and then methanol was distilled off. The residue was dissolved in water, and the solution was washed with ethyl acetate. To the aqueous solution was added ethyl acetate, and the mixture was adjusted to pH 2 with 10% hydrochloric acid, and then the ethyl acetate layer was separated from the mixture. The remaining aqueous layer was saturated with sodium chloride and then extracted with ethyl acetate. The ethyl acetate extract was combined with the separated ethyl acetate layer, washed with a saturated aqueous solution of sodium chloride and then dried. The solvent was distilled off, and the residue was washed with diethyl ether and then dried to give 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-propanesulfonylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid, which can be represented as 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-propanesulfonylimino-2,3-dihydro-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid, (5.5 g.), mp. 160° to 170° C. (dec.).

Workup

  1. additionwas dropwise added
  2. temperatureice-cooling
  3. stirringThe mixture was further stirred for 1 hour
  4. distillationmethanol was distilled off
  5. dissolutionThe residue was dissolved in water
  6. washthe solution was washed with ethyl acetate
  7. additionTo the aqueous solution was added ethyl acetate
  8. customthe ethyl acetate layer was separated from the mixture
  9. extractionextracted with ethyl acetate
  10. extractionThe ethyl acetate extract
  11. washwashed with a saturated aqueous solution of sodium chloride
  12. customdried
  13. distillationThe solvent was distilled off
  14. washthe residue was washed with diethyl ether
  15. customdried

Sources & evidence

ORD record
ord-80a9a42335e44b50b94dd718e401fa96
Source dataset
uspto-grants-1984_04
Patent number
US04440766

Reaction notes

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