Water → HCID 19973447, compound

HRID 1440250Notes

Reaction equation

HRID 1440250 reaction equation
[CH3:1][NH:2][C:3]([C:5]1([N:12]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[N:14]=[CH:13]2)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])=[S:4].[BH4-].[Na+].[Cl-].[NH4+].O>CO>[OH:11][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:5]1([N:12]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[N:14]=[CH:13]1)[C:3](=[S:4])[NH:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 19973438HCID 19973438, compound

Product 1

HCID 19973447HCID 19973447, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 56.89 g (202 mmol) of the N-methyl-1-(4-nitroimidazol-1-yl)-2-oxocyclohexanecarbothioamide prepared in the Example 16 in 640 ml of methanol was cooled with ice. 2.68 g (70.8 mmol) of sodium borohydride was added to the resulting suspension in portions in 3 minutes in such a way that the bulk temperature did not exceed 10° C. The obtained mixture was stirred under cooling with ice for 30 minutes, followed by the addition of a saturated aqueous solution of ammonium chloride and water in this order. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt and dried over anhydrous magnesium sulfate. The resulting organic phase was analyzed by silica gel thin-layer chromatography [developer: benzene/ethyl acetate (1:2)], by which it was ascertained that the product of this stage was composed of a lowly polar diastereomer (L form. Rf: 0.41) and a highly polar diastereomer (M form. RF: 0.29) at a ratio of 2:1. The organic phase was concentrated. In the course of this concentration, a crystal began to precipitate. The crystal thus formed was recovered by filtration. Thus, 28.48 g of the title compound was obtained in the form of a diastereomer as a pale-yellow crystal (yield: 50%).

Workup

  1. temperaturewas cooled with ice
  2. customdid not exceed 10° C
  3. temperatureunder cooling with ice for 30 minutes
  4. extractionThe obtained mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with a saturated aqueous solution of common salt
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe organic phase was concentrated
  8. concentrationIn the course of this concentration
  9. customto precipitate
  10. customThe crystal thus formed
  11. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-2e90a639a471442ba10e447801db23b5
Source dataset
uspto-grants-1996_03
Patent number
US05498634

Reaction notes

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