Sodium borohydride → HCID 11463158, compound

HRID 2216635Notes

Reaction equation

HRID 2216635 reaction equation
[C:1]([C:4]1[O:8][C:7]([NH:9][C:10](=[O:27])[CH:11]([NH:15][C:16](=[O:26])[CH2:17][C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.C1COCC1>[OH:3][CH:1]([C:4]1[O:8][C:7]([NH:9][C:10](=[O:27])[CH:11]([NH:15][C:16](=[O:26])[CH2:17][C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11268961HCID 11268961, compound

Product 1

HCID 11463158HCID 11463158, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid (5-acetyl-oxazol-2-yl)-amide (130 mg, 0.34 mmol) in a mixture of MeOH (5 ml) and THF (5 mL) was added NaBH4 (130 mg, 3.9 mmol) at room temperature. After stirring for 10 min, the mixture was concentrated to a small volume, quenched with water and extracted with methylene chloride. The organic layer was separated, dried and concentrated to give 131 mg of the title compound as a colorless oil. LC-MS, RT=1.7 min, M+1=382.2, M−1=380.2.

Workup

  1. concentrationthe mixture was concentrated to a small volume
  2. customquenched with water
  3. extractionextracted with methylene chloride
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-235ab5dff4274e05b48a42e40a08b21a
Source dataset
uspto-grants-2006_09
Patent number
US07112599B2

Reaction notes

Loading…