Hydrochloric Acid → [4-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester

HRID 1767874노트

반응식

HRID 1767874 반응식
[H-].[Na+].[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)([CH3:6])([CH3:5])[CH3:4].[C:20]([O:24][C:25](=[O:28])[CH2:26]Br)([CH3:23])([CH3:22])[CH3:21].Cl>CN(C)C=O>[C:20]([O:24][C:25](=[O:28])[CH2:26][N:13]1[C:14]2[C:10](=[C:9]([O:8][Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:19])[CH3:18])[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1)([CH3:23])([CH3:22])[CH3:21]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 115939764-(t-Butyldimethylsilyloxy)indole

생성물 1

HCID 69283774[4-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A dispersion of sodium hydride in mineral oil (55%, 61 mg, 1.4 mmol) was added to a solution of 4-(tert-butyl-dimethyl-silanyloxy)-1H-indole [251 mg, 1 mmol; Eur. Pat. Appl. (1986), EP 206225 A2] and bromo-acetic acid tert-butyl ester (160 μl. 1, 1.1 mmol) in N,N-dimethylformamide (10 ml) at 0° C. under an argon atmosphere. The reaction mixture was naturally warmed to ambient temperature, stirred for 14 h and cooled to 0° C. Ice water (10 ml) and concentrated HCl (2 ml) were added and the mixture was extracted three times with dichloromethane. The combined extracts were washed with brine and water and dried over sodium sulfate. The solvent was removed under reduced pressure to give a yellow liquid which was purified by column chromatography (silica gel, heptane/AcOEt) to give 246 mg (0.68 mmol, 67%) of the title compound as light yellow oil.

후처리

  1. temperaturecooled to 0° C
  2. extractionthe mixture was extracted three times with dichloromethane
  3. washThe combined extracts were washed with brine and water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customto give a yellow liquid which
  7. customwas purified by column chromatography (silica gel, heptane/AcOEt)

출처 및 근거

ORD 기록
ord-aaf3dae49dd14832952ae8f3331f6b8b
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235572B2

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