Sodium hydride → 1,2-dibenzyl 1-tert.butyl 4-methyl-1-[(1,2-dimethyl-3,5-dioxo-1,2,4-triazolidin-4-yl)methyl]-1,1,2(R)-pentanetricarboxylate

HRID 2399228노트

반응식

HRID 2399228 반응식
[H-].[Na+].[CH3:3][CH:4]([CH3:35])[CH2:5][C@@H:6]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Br[CH2:37][N:38]1[C:42](=[O:43])[N:41]([CH3:44])[N:40]([CH3:45])[C:39]1=[O:46]>CN(C)C=O>[CH3:3][CH:4]([CH3:35])[CH2:5][C@@H:6]([C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[C:7]([CH2:37][N:38]1[C:42](=[O:43])[N:41]([CH3:44])[N:40]([CH3:45])[C:39]1=[O:46])([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 18660804Dibenzyl 3(RS)-tert-butoxycarbonyl-2(R)-isobutylsuccinateHCID 193868174-Bromomethyl-1,2-dimethylurazole

생성물 1

HCID 700435121,2-dibenzyl 1-tert.butyl 4-methyl-1-[(1,2-dimethyl-3,5-dioxo-1,2,4-triazolidin-4-yl)methyl]-1,1,2(R)-pentanetricarboxylate수율 62.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

0.284 g of 60% sodium hydride was added to a stirred ice-cold solution of 3.01 g of 1,2-dibenzyl 1-tert.butyl 4-methyl-1,1,2(R)-pentanetricarboxylate in 50 ml of dry dimethylformamide under a nitrogen atmosphere. The mixture was stirred for 30 minutes at 0° and for an additional 1.5 hours at ambient temperature, and again cooled to 0° before the addition of 1.6 g of 4-bromomethyl-1,2-dimethylurazole. The mixture was allowed to return to ambient temperature and was stirred for 3 hours. The volatiles were evaporated under high vacuum and the residue was dissolved in ethyl acetate and washed with 5% aqueous citric acid solution, water and saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the residue was purified by flash chromatography on silica gel using hexane/ether (1:1) followed by ether for the elution. There were obtained 2.464 g of 1,2-dibenzyl 1 -tert.butyl 4-methyl-l-[(1,2-dimethyl-3,5-dioxo-1,2,4-triazolidin-4-yl) methyl]-1,1,2(R)-pentanetricarboxylate in the form of a colorless oil.

후처리

  1. customto return to ambient temperature
  2. stirringwas stirred for 3 hours
  3. customThe volatiles were evaporated under high vacuum
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with 5% aqueous citric acid solution, water and saturated sodium chloride solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customthe residue was purified by flash chromatography on silica gel
  9. washfollowed by ether for the elution

출처 및 근거

ORD 기록
ord-0ff4184a887941ab9f62e3023aca7990
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05447929

반응 노트

불러오는 중…