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Imidazole → (R)-Toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester

HRID 495715
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HRID 495715 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:21])[CH2:9][O:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C(OCC)(=O)C>CN(C)C=O>[C:30]([Si:27]([CH3:29])([CH3:28])[O:21][C@H:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:9][O:10][S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1)(=[O:13])=[O:12])([CH3:33])([CH3:32])[CH3:31]
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참가 물질

6

반응물 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 11738935(R)-Toluene-4-sulfonic acid 2-(6-chloro-pyridin-3-yl)-2-hydroxy-ethyl ester

생성물 1

HCID 12972452(R)-Toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester수율 84.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a cooled (50° C.), stirred solution of (R)-toluene-4-sulfonic acid 2-(6-chloro-pyridin-3-yl)-2-hydroxy-ethyl ester (4.9 g) and imidazole (2.0 g) in anhydrous dimethyformamide (14 mL) was added t-butyldimethylsilyl chloride (2.8 g). The reaction mixture was allowed to warm to room temperature and stirring was continued for 18 h. Ethyl acetate was added, followed by washing with water (2×), drying over sodium sulfate and concentration in vacuo to afford an oil. Chromatography (Flash 40M®) utilizing 10% ethyl acetate/hexanes afforded 5.6 g of the title compound (I-2e) as a colorless oil.

후처리

  1. temperatureto warm to room temperature
  2. washby washing with water (2×)
  3. dry with materialdrying over sodium sulfate and concentration in vacuo
  4. customto afford an oil

출처 및 근거

ORD 기록
ord-46e54779df7f45b28353f87dace4c1ad
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06939867B2

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