Sodium borohydride → HCID 22349654, compound

HRID 896267Notes

Reaction equation

HRID 896267 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:26])[C:11](=[O:25])[C:12]2[S:16][C:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:26])[CH:11]([C:12]2[S:16][C:15]([NH:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[N:14][CH:13]=2)[OH:25])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22349643HCID 22349643, compound

Product 1

HCID 22349654HCID 22349654, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(3,4-difluorophenyl)-2-(2-tert-butoxycarbonylamino-1,3-thiazole-5-yl) (oxo)acetamide (938 mg, 2.4 mmol) in THF (50 ml) and MeOH (10 ml) was treated with sodium borohydride (93 mg, 2.4 mmol) for 30 minutes. The mixture was evaporated, the residue dissolved in ethanol (3 ml) water (25 ml) was added, and the pH adjusted to 6, more water was added, a solid was recovered, dried, recristalized in ether/petroleum ether to give title compound (850 mg, 90%).

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue dissolved in ethanol (3 ml) water (25 ml)
  3. additionwas added
  4. additionwas added
  5. customa solid was recovered
  6. customdried

Sources & evidence

ORD record
ord-0f7cae1caebe4c1db1cc6e50291a5d06
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

Loading…