Water → Benzyl 3-(1-ethyl-2-oxo-2,3-dihydro-1H-benzimidazol-4-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176612노트

반응식

HRID 1176612 반응식
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][O:13][CH:14]3[CH:19]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[O:38][CH3:39])=[CH:22][CH:21]=4)[CH2:18][CH2:17][N:16]([C:40]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])[CH2:15]3)[C:6]=2[N:5](COCC[Si](C)(C)C)[C:4]1=[O:58])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][O:13][CH:14]3[CH:19]([C:20]4[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[O:38][CH3:39])=[CH:24][CH:25]=4)[CH2:18][CH2:17][N:16]([C:40]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])[CH2:15]3)[C:6]=2[NH:5][C:4]1=[O:58])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 68501198benzyl 3-[1-ethyl-2-oxo-3-(2-trimethylsilanylethoxymethyl)-2,3-dihydro-1H-benzimidazol-4-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

생성물 1

HCID 68501932Benzyl 3-(1-ethyl-2-oxo-2,3-dihydro-1H-benzimidazol-4-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 0.310 g of benzyl 3-[1-ethyl-2-oxo-3-(2-trimethylsilanylethoxymethyl)-2,3-dihydro-1H-benzimidazol-4-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 4 ml of tetrahydrofuran is admixed with 6 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran). The reaction solution is heated to reflux over 48 hours, subsequently cooled to room temperature and admixed with 40 ml of water. The mixture is extracted with tert-butyl methyl ether (2×40 ml) and the combined organic phases are washed with 40 ml of brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.18 (3:1 EtOAc-heptane); Rt=5.66.

후처리

  1. temperatureThe reaction solution is heated
  2. temperatureto reflux over 48 hours
  3. extractionThe mixture is extracted with tert-butyl methyl ether (2×40 ml)
  4. washthe combined organic phases are washed with 40 ml of brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-8103e0695e77469788230d6372aed61e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

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