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Sodium hydride → (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-methyl-N-(4-trifluoromethoxybenzyl)carbamate

HRID 856184
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HRID 856184 반응식
[H-].[Na+].[CH3:3][N:4]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1)[C:5](=[O:21])[O:6][CH2:7][C@@:8]([OH:20])([CH3:19])[CH2:9][N:10]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[N:12]=[C:11]1Cl>CN(C=O)C>[CH3:3][N:4]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1)[C:5](=[O:21])[O:6][CH2:7][C@:8]1([CH3:19])[O:20][C:11]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:10]2[CH2:9]1
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참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 69481203(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxybenzyl)carbamate

생성물 1

HCID 69481462(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-methyl-N-(4-trifluoromethoxybenzyl)carbamate수율 55.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (0.28 g, 7.04 mmol) was added to a solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxybenzyl)carbamate prepared in Example 72 (2.74 g, 5.87 mmol) in DMF (20 ml) followed by stirring for 1 hour with cooling on ice-bath. To the reaction mixture, ice-water was added, and the precipitates were filtered off, washed with water and then recrystallized from isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-methyl-N-(4-trifluoromethoxybenzyl)carbamate (1.40 g, yield 55%) as a white solid.

후처리

  1. temperaturewith cooling on ice-bath
  2. filtrationthe precipitates were filtered off
  3. washwashed with water
  4. customrecrystallized from isopropanol

출처 및 근거

ORD 기록
ord-8b53b1c606c94d488a0b1500b3ea520c
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262212B2

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