Methanol → HCID 70489781, compound

HRID 638452Notes

Reaction equation

HRID 638452 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:30])[C:22]([C:24]4[NH:25][C:26](=[O:29])[S:27][CH:28]=4)=[O:23])[C:18](=[O:31])[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:30])[CH:22]([OH:23])[C:24]4[NH:25][C:26](=[O:29])[S:27][CH:28]=4)[C:18](=[O:31])[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 borohydride2×HCID 70505148HCID 70505148, compoundHCID 178482022HCID 178482022, compound

Product 1

HCID 70489781HCID 70489781, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-(2-oxo-2,3-dihydro-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-hydroxy-1,3-thiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, (5.2 g.), methanol (200 ml.) and 1N sodium hydroxide aqueous solution (10.8 ml.) was dropwise added a mixture of sodium borohydride (0.205 g.) and ethanol (8 ml.) over 10 minutes at 5° to 10° C. with stirring. The mixture was further stirred for 20 minutes at the same temperature, and then a mixture of sodium borohydride (0.01 g.) and ethanol (0.5 ml.) was further added thereto at the same temperature. The mixture was further stirred for 30 minutes at the same temperature, and then the reaction mixture was concentrated under reduced pressure. To the residue was added water (200 ml.), and the solution was washed with ethyl acetate. The aqueous solution was adjusted to pH 5 with 10% hydrochloric acid and washed with ethyl acetate. The solution was adjusted to pH 1 with 10% hydrochloric acid and extracted with ethyl acetate. The remaining aqueous layer was subjected to salting-out and then further extracted with ethyl acetate. The ethyl acetate extracts were combined together, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then treated with activated charcoal. The solvent was distilled off, and the residue was pulverized in diethyl ether, collected by filtration and then dried to give pale yellow powder of 3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-7-[2-hydroxy-2-(2-oxo-2,3-dihydro-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-hydroxy-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid, (3.6 g.), mp. 110° to 121° C. (dec.).

Workup

  1. additionwas dropwise added
  2. stirringThe mixture was further stirred for 20 minutes at the same temperature
  3. additionwas further added
  4. stirringThe mixture was further stirred for 30 minutes at the same temperature
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. additionTo the residue was added water (200 ml.)
  7. washthe solution was washed with ethyl acetate
  8. washwashed with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. extractionfurther extracted with ethyl acetate
  11. washwashed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. additiontreated with activated charcoal
  14. distillationThe solvent was distilled off
  15. filtrationcollected by filtration
  16. customdried

Sources & evidence

ORD record
ord-a6b7fc481eb047c4a828d700df4d8ce6
Source dataset
uspto-grants-1985_12
Patent number
US04560765

Reaction notes

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