1H-1,2,4-Triazole → 1-(((2R,3S)-2-(2,5-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole

HRID 1250381Notes

Reaction equation

HRID 1250381 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@:9]([OH:21])([C@H:15](S(C)(=O)=O)[CH3:16])[CH2:10]S(C)(=O)=O.[NH:22]1[CH:26]=[N:25][CH:24]=[N:23]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@:9]1([CH2:10][N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)[C@H:15]([CH3:16])[O:21]1

Participants

3

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 69942689(2R,3R)-2-(2,5-difluorophenyl)-1,3-bis(methanesulfonyl)-2-butanol

Product 1

HCID 101311921-(((2R,3S)-2-(2,5-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazoleYield 56%

Procedure

In the same manner as that described in Example 7(iv) above, 7.00 g (18.7 mmol) of (2R,3R)-2-(2,5-difluorophenyl)-1,3-bis(methanesulfonyl)-2-butanol [prepared as described in Step 8(iii) above] were reacted with 1H-1,2,4-triazole and the reaction product was purified by chromatography on a silica gel (100 g) column using a 1:1 to 3:2 mixture of ethyl acetate and hexane as the eluant to afford 2.65 g (yield 56%) of the title compound as an oil.

Workup

  1. customthe reaction product was purified by chromatography on a silica gel (100 g) column
  2. additionto 3:2 mixture of ethyl acetate and hexane as the eluant

Sources & evidence

ORD record
ord-9d9fc272dd8a40498265342d68caa73c
Source dataset
uspto-grants-2002_01
Patent number
US06337403B1

Reaction notes

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