Sodium borohydride → HCID 11281965, compound

HRID 2216634Notes

Reaction equation

HRID 2216634 reaction equation
C([O:3][C:4]([C:6]1[O:10][C:9]([NH:11][C:12](=[O:29])[CH:13]([NH:17][C:18](=[O:28])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH2:14][CH2:15][CH3:16])=[N:8][C:7]=1[C:30]([F:33])([F:32])[F:31])=O)C.[BH4-].[Na+]>CO>[OH:3][CH2:4][C:6]1[O:10][C:9]([NH:11][C:12](=[O:29])[CH:13]([NH:17][C:18](=[O:28])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH2:14][CH2:15][CH3:16])=[N:8][C:7]=1[C:30]([F:32])([F:31])[F:33]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69356721HCID 69356721, compound

Product 1

HCID 11281965HCID 11281965, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-{2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoylamino}-4-trifluoromethyl-oxazole-5-carboxylic acid ethyl ester (150 mg, 0.31 mmol) and sodium borohydride (150 mg, 3.947 mmol) in 3 ml methanol was stirred at room temperature for 10 min. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated and the residue was purified by preparative HPLC to give the title compound as a white solid. APCl M+1=436.1.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-bc79726595c84556b8cf5e03b0c210ef
Source dataset
uspto-grants-2006_09
Patent number
US07112599B2

Reaction notes

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