Water → 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-formyl-indole-1-carboxylic acid tert-butyl ester

HRID 2078689노트

반응식

HRID 2078689 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:19]1[C:20]2[S:33][CH:32]=[CH:31][C:21]=2[N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[N:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O.C(OCC)(=O)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:19]1[C:20]2[S:33][CH:32]=[CH:31][C:21]=2[N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[N:23]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 576372852-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester2회

생성물 1

HCID 576373352-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-formyl-indole-1-carboxylic acid tert-butyl ester수율 81%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester [373 mg, 0.794 mmol Intermediate (10)] in Dichloromethane (20 mL) is added Dess-Martin Periodinane (407 mg, 0.959 mmol). Stirred at room temperature for 30 minutes. Water (10 mL) is added and stirred for 30 minutes at room temperature. The reaction mixture is dissolved with ethyl acetate (30 mL) and washed twice with a mixture of 10% Na2S2O3/saturated NaHCO3 (4 mL) solution. The ethyl acetate phase is washed with water, NaHCO3, brine and dried over sodium sulfate. The residue is chromatographed on 10 g silica gel cartridge eluting with 30 to 40% ethyl acetate gradient in heptane to afford 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-formyl-indole-1-carboxylic acid tert-butyl ester [300 mg, 81%, Intermediate (11)] as a white solid; 1H NMR [(CD3)2SO)]: δ 10.079 (1H, s, CHO), 8.323 (1H, s), 8.318 (1H, d), 8.017 (1H, s), 7.978 (1H, d), 7.391 (1H, d), 7.345 (1H, s), 1.660 (9H, s), 1.341 (9H, s); TLC data Rf=0.37 (30% ethyl acetate in heptane).

후처리

  1. stirringstirred for 30 minutes at room temperature
  2. washwashed twice with a mixture of 10% Na2S2O3/saturated NaHCO3 (4 mL) solution
  3. washThe ethyl acetate phase is washed with water, NaHCO3, brine
  4. dry with materialdried over sodium sulfate
  5. customThe residue is chromatographed on 10 g silica gel cartridge
  6. washeluting with 30 to 40% ethyl acetate gradient in heptane

출처 및 근거

ORD 기록
ord-ecb247eec5094146bc8e615a16d4d6ac
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928231B2

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