Hydrogen Peroxide → Dibenzyl 2-(2,4-difluorophenyl)-1-{3-[(E)-4-(2,2,3,3-tetrafluoropropoxy)styryl]-1H-1,2,4-triazol-1-yl}-3-(1H-1,2,4-triazol-1-yl)-2-propyl phosphate

HRID 489475ノート

反応式

HRID 489475 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:38])([CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1)[CH2:10][N:11]1[CH:15]=[N:14][C:13](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:20][CH:19]=2)=[N:12]1.N1C=NN=N1.C(N(C(C)C)[P:48]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(C)C.[OH:68]O>C(Cl)Cl>[P:48]([O:38][C:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1)[CH2:10][N:11]1[CH:15]=[N:14][C:13](/[CH:16]=[CH:17]/[C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]([F:31])([F:30])[CH:27]([F:28])[F:29])=[CH:22][CH:23]=2)=[N:12]1)([O:49][CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)([O:57][CH2:58][C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)=[O:68]

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 196621Bis(benzyloxy)(diisopropylamino)phosphineHCID 10030147(E)-(+)-2-(2,4-Difluorophenyl)-1-{3-[4-(2,2,3,3-tetrafluoropropoxy)styryl]-1H-1,2,4-triazol-1-YL}-3-(1H-1,2,4-triazol-1-YL)propan-2-OLHCID 178418441HCID 178418441、化合物

生成物 1

HCID 22266795Dibenzyl 2-(2,4-difluorophenyl)-1-{3-[(E)-4-(2,2,3,3-tetrafluoropropoxy)styryl]-1H-1,2,4-triazol-1-yl}-3-(1H-1,2,4-triazol-1-yl)-2-propyl phosphate収率 84%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2-(2,4-Difluorophenyl)-1-{3-[(E)-4-(2,2,3,3-tetrafluoropropoxy)styryl]-1H-1,2,4-triazol-1-yl}-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (the racemate of Example 19, EP 0472392, 475 mg, 0.88 mmol), 1H-tetrazole (185 mg, 2.64 mmol) and dibenzyl diisopropylphosphoramidite (607 mg, 1.76 mmol) in methylene chloride (5 ml) was stirred at room temperature under a nitrogen atmosphere for 20 hours. The mixture was then cooled to 0° C., and hydrogen peroxide (1.0 ml, 30% solution in water) was added dropwise maintaining the temperature below 20° C. The resulting mixture was stirred at 20° C. for 30 minutes before separating the organic layer, which was washed with water, dried (MgSO4) and the solvent evaporated. The resulting pale yellow oil was purified by column chromatography (silica gel, eluting with ethyl acetate/hexane) to give the subtitle compound as a viscous syrup (595 mg, 84%).

後処理

  1. temperaturemaintaining the temperature below 20° C
  2. custombefore separating the organic layer, which
  3. washwas washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated
  6. customThe resulting pale yellow oil was purified by column chromatography (silica gel, eluting with ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-7e951a8cabcf4f9c82233310d5116b52
出典データセット
uspto-grants-2005_12
特許番号
US06977302B2

反応ノート

読み込み中…