Water → HCID 178451419、化合物

HRID 1846814ノート

反応式

HRID 1846814 の反応式
[C:1]([O:5][C:6](O[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][CH:24]1[CH2:27][CH:26]([C:28]2[NH:32][C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[N:29]=2)[CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.ClCCl>[CH2:16]([O:23][C@@H:24]1[CH2:25][C@H:26]([C:28]2[N:29]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=2)[CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[CH2:16]([O:23][C@H:24]1[CH2:25][C@H:26]([C:28]2[N:29]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=2)[CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 674813742-(3-(Benzyloxy)cyclobutyl)-1H-benzo[d]imidazole

生成物 2

HCID 178451418HCID 178451418、化合物収率 33%HCID 178451419HCID 178451419、化合物収率 36%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

DMAP (0.020 g, 0.16 mmol) and di-tert-butyldicarbonate (0.83 g, 3.77 mmol) were added to a suspension of 2-(3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole (0.96 g, 3.43 mmol) and triethylamine (1.20 mL, 8.58 mmol) in dichloromethane (15 mL) and the mixture was stirred for 16 h. Water was added, the resulting layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil. The oil was purified by silica gel chromatography to give tert-butyl 2-(cis-3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.43 g, 1.14 mmol, 33% yield) and tert-butyl 2-(trans-3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.47 g, 1.23 mmol, 36% yield).

後処理

  1. customthe resulting layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-79b2e34ebfbd4da7b5cd48404d1fa16e
出典データセット
uspto-grants-2015_02
特許番号
US08952037B2

反応ノート

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