2-Dimethylaminopyridine → (αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-methyl-1H-1,2,4-triazole-1-butanamide

HRID 1241927Notes

Reaction equation

HRID 1241927 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@:9]1([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[O:12][C:11](=[O:13])[C@@H:10]1[CH3:14].C[N:22](C1C=CC=CN=1)C>N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@:9]([OH:12])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C@@H:10]([CH3:14])[C:11]([NH2:22])=[O:13]

Participants

4

Reactant 2

HCID 218852-DimethylaminopyridineHCID 58224186HCID 58224186, compound

Product 1

HCID 58224182(αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-methyl-1H-1,2,4-triazole-1-butanamideYield 5,096.7%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

7.1 g (25.4 mmol) of (3R,4R)-4-(2,5-difluorophenyl)-3-methyl-4-[1,2,4]triazol-1-ylmethyl-oxetan-2-one were dissolved in 250 ml aqueous ammonia (NH4OH 25%) and, after the addition of 64 mg (0.5 mmol) of dimethylaminopyridine, were stirred for 1 hour at room temperature. Evaporation of the reaction mixture gave crude 7.55 g (100% yield) of (2R,3R)-3-(2,5-difluoro-phenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-yl-butyramide.

Workup

  1. customEvaporation of the reaction mixture

Sources & evidence

ORD record
ord-95dcb85cd27c425d9da729027b7ec0a7
Source dataset
uspto-grants-2006_10
Patent number
US07115643B2

Reaction notes

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