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2-Bromoethanol → (S)-5-{(3,5-Bis-trifluoromethyl-benzyl)-(2-(2-hydroxy-ethyl)-2H-tetrazol-5-yl)-amino}-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester

HRID 507044
ノート
印刷プレビュー

反応式

HRID 507044 の反応式
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:6][N:7]([C:31]1[N:32]=[N:33][NH:34][N:35]=1)[C@H:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]2[CH:22]=[C:23]([C:27]([F:30])([F:29])[F:28])[C:24]([CH3:26])=[CH:25][C:9]1=2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:52][CH2:53][OH:54]>CN(C=O)C>[C:18]([O:17][C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:8]([N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:43])([F:1])[F:44])[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=2)[C:31]2[N:32]=[N:33][N:34]([CH2:52][CH2:53][OH:54])[N:35]=2)[C:9]2[CH:25]=[C:24]([CH3:26])[C:23]([C:27]([F:28])([F:29])[F:30])=[CH:22][C:10]1=2)=[O:16])([CH3:20])([CH3:21])[CH3:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 59432487(S)-tert-Butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2H-tetrazol-5-yl)amino)-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

生成物 1

HCID 59432357(S)-5-{(3,5-Bis-trifluoromethyl-benzyl)-(2-(2-hydroxy-ethyl)-2H-tetrazol-5-yl)-amino}-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester収率 26%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Dissolve (S)-tert-Butyl 5-[(3,5-bistrifluoromethylbenzyl)-(2H-tetrazol-5-yl)amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (Example 3, Step 16) (0.252 g, 0.395 mmole) in DMF (4 mL), add potassium carbonate (0.0929 g, 0.672 mmole) in one portion. Inject 2-bromoethanol (0.0420 mL, 0.593 mmole) dropwise. Stir at room temperature overnight. Partition the reaction mixture between ethyl acetate (50 mL) and water (50 mL). Extract aqueous back with more ethyl acetate (20 mL). Combine organic layers, Dry over sodium sulfate, filter and concentrate the solution. Chromatograph the residue over silica gel, eluting with ethyl acetate/hexanes (0-100%), to provide the title compound as a colorless oil (0.0700 g, 26%). MS (ES+): 705 (M+Na).

後処理

  1. customPartition the reaction mixture between ethyl acetate (50 mL) and water (50 mL)
  2. dry with materialCombine organic layers, Dry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate the solution
  5. washChromatograph the residue over silica gel, eluting with ethyl acetate/hexanes (0-100%)

出典と根拠

ORDレコード
ord-b3c5d31a46d14241a7be5ca803d59cee
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07786108B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート