Diethyl Ether → (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclopentyl-methanone

HRID 2075030노트

반응식

HRID 2075030 반응식
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[CH:25]([CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[OH:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC.[OH-].[Na+]>C(Cl)Cl>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:34]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 58968659(2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclopentyl-methanol

생성물 1

HCID 58968713(2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclopentyl-methanone수율 94%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclopentyl-methanol (44,5 mg, 0.077 mmol) in methylene chloride (1.0 mL) at room temperature was added Dess-Martin periodinane reagent (35.7 mg, 0.084 mmol). The mixture was stirred at room temperature for 1.5 hours. Ether and 1N sodium hydroxide was added. The mixture was extracted with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to yield a pale yellow oil (41.6 mg, 94%). 1H NMR (400 MHz, CDCl3) δ ppm 1.58-1.72 (m, 4H) 1.75-1.88 (m, 4H) 3.48-3.58 (m, 1H) 4.18 (s, 3H) 4.81 (s, 2H) 4.88 (s, 2H) 7.53 (s, 1H) 7.57 (d, J=8.30 Hz, 1H) 7.66 (s, 2H) 7.71 (d, 1H) 7.73 (s, 1H). MS (ES+) Calc: 579.2, Found: 580.4 (M+1).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washCombined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-85cdb22aecfa431d938bf301d5d92b92
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919506B2

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