Sodium borohydride → HCID 58033108, compound

HRID 533967Notes

Reaction equation

HRID 533967 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:22])[CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH3:15])=[N:8][CH:7]=1)=[O:5].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH:4]([OH:5])[C:6]1[S:10][C:9]([NH:11][C:12](=[O:22])[CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH3:15])=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 58033030HCID 58033030, compound

Product 1

HCID 58033108HCID 58033108, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[5-(2-Chloro-benzoyl)-thiazol-2-yl]-2-phenyl-butyramide (102 mg, 0.265 mmol) was suspended in 1 mL of anhydrous methanol. Sodium borohydride (30.3 mg, 0.801 mmol) was slowly added and the resulting pale yellow solution was allowed to stir for 1 hour at room temperature. After stirring for one hour a second aliquot of sodium borohydride (30.3 mg, 0.801 mmol) was added. The reaction mixture was allowed to stir for an additional hour and then the crude product was evaporated to dryness and then dissolved in a minimum of ethyl acetate. The organic layer was washed three times with an equal volume of 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was then dried over sodium sulfate, filtered, and evaporated to dryness. The crude product was further purified by reverse-phase preparative liquid chromatography to yield the pure product (46 mg, 0.12 mmol, 45%) ESI-MS m/z calc. 386.1. found 387.3 (M+1)+ Retention time 3.83 minutes.

Workup

  1. additionwas added
  2. stirringto stir for an additional hour
  3. customthe crude product was evaporated to dryness
  4. dissolutiondissolved in a minimum of ethyl acetate
  5. washThe organic layer was washed three times with an equal volume of 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  6. dry with materialThe organic layer was then dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe crude product was further purified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-185dea4c86e34de890a6d6a57e5c7b8b
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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