(2R, 3S)-N-[(tert-Butyloxy)carbonyl]-3-amino-4-phenyl-2-(triisopropylsilyloxy) butan-1-ol → (2R 3S)-N-[(tert-butyloxy)carbonyl]-3-amino-2-(triisopropylsilyloxy)-4-cyclohexyl-1-butanol

HRID 326319

반응식

HRID 326319 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:10]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Rh]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[C@@H:10]([O:13][Si:14]([CH:15]([CH3:16])[CH3:17])([CH:18]([CH3:19])[CH3:20])[CH:21]([CH3:22])[CH3:23])[CH2:11][OH:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 1

HCID 15281982(2R, 3S)-N-[(tert-Butyloxy)carbonyl]-3-amino-4-phenyl-2-(triisopropylsilyloxy) butan-1-ol

생성물 1

HCID 15281983(2R 3S)-N-[(tert-butyloxy)carbonyl]-3-amino-2-(triisopropylsilyloxy)-4-cyclohexyl-1-butanol수율 67%

시약·촉매·용매 2

HCID 887Methanol용매HCID 23948Rhodium용매

실험 절차

The alcohol of Step 2 (12.8 g, 29.3 mmol) was dissolved in MeOH (135 mL) and hydrogenated with 5% Rh/C at 60 psi and 60° C. for 30 hours. The filtrate was concentrated and purified by medium pressure column chromatography (silica gel, 15% ethyl acetate in hexane) to give the title compound as a white solid (8.70 g, 67% yield, mp 61°-63° C.). Anal. calcd. for C24H49NO4Si: C, 64.96; H, 11.13; N, 3.16. Found: C, 65.16; H, 11.26; N, 3.12.

후처리

  1. concentrationThe filtrate was concentrated
  2. custompurified by medium pressure column chromatography (silica gel, 15% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-8540141bfee04d2789eeddbab69250a4
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05268391

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