Diisobutylaluminum hydride → Tert-butyl 2-hydroxy-1-((phenylthio)methyl)ethylcarbamate

HRID 1785794노트

반응식

HRID 1785794 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18](OC)=[O:19])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:19][CH2:18][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 18637399Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

생성물 1

HCID 13969831Tert-butyl 2-hydroxy-1-((phenylthio)methyl)ethylcarbamate

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of Example 175A (1.22 g, 3.91 mmol) in toluene (10 mL) at −78° C. was treated with 1M DIBAL-H in toluene (8.6 mL), warmed to room temperature over 4 hours, diluted with ethyl acetate (100 mL), washed sequentially with 0.1N HCl (30 mL), water (15 mL), and brine (50 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product. MS (DCI) m/e 284 (M+H)+.

후처리

  1. washwashed sequentially with 0.1N HCl (30 mL), water (15 mL), and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-d538eb01bc4842b685617d6d5a94c62a
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504512B2

반응 노트

불러오는 중…