Water → tert-butyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate

HRID 856302ノート

反応式

HRID 856302 の反応式
Cl[C:2]1[N:3]([CH2:10][C@:11]([OH:27])([CH3:26])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+].C(OCC)(=O)C.O>CN(C=O)C>[CH3:26][C@@:11]1([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[O:27][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69635130tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate

生成物 1

HCID 69635111tert-butyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate収率 71%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate prepared in Example 365 (10.25 g, 25.4 mmol) was dissolved in DMF (30 ml). To the solution, sodium hydride (1.12 g, 27.9 mmol) was added followed by stirring for 2 hours with cooling on ice-bath. To the reaction mixture, ethyl acetate (10 ml) and water (70 ml) were added. The precipitates were filtered off, and washed with water. The crude solids were recrystallized from ethyl acetate (70 ml) to afford tert-butyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (6.62 g, yield 71%) as a light yellow powder.

後処理

  1. temperaturewith cooling on ice-bath
  2. filtrationThe precipitates were filtered off
  3. washwashed with water
  4. customThe crude solids were recrystallized from ethyl acetate (70 ml)

出典と根拠

ORDレコード
ord-81ba49631f4c483098d27ec0a3343295
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

反応ノート

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