(2S)-2-amino butanic acid t-butyl ester → (s)-2-[3-(1-Tertbutoxycarbonyl-propylamino)-7-chloro-1-oxo-3,4-dihydro-1h-isoquinolin-2-yl]-butyric acid tert-butyl ester

HRID 1091427노트

반응식

HRID 1091427 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7]O[C:9]2=[O:12])=[CH:4][CH:3]=1.[NH2:13][C@@H:14]([CH2:22][CH3:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>>[C:18]([O:17][C:15](=[O:16])[C@@H:14]([N:13]1[CH:7]([NH:13][CH:14]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:22][CH3:23])[CH2:6][C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]1=[O:12])[CH2:22][CH3:23])([CH3:19])([CH3:21])[CH3:20]

참가 물질

3

반응물 2

HCID 7019938(2S)-2-amino butanic acid t-butyl esterHCID 116440287-chloro-1H-isochromen-1-one

생성물 1

HCID 66593868(s)-2-[3-(1-Tertbutoxycarbonyl-propylamino)-7-chloro-1-oxo-3,4-dihydro-1h-isoquinolin-2-yl]-butyric acid tert-butyl ester수율 64.2%

반응 조건

온도
85 °C

실험 절차

A mixture of 7-chloro-isochromen-1-one (10 g) and (S)-2-aminobutyric acid, tert butyl ester (22 g) were heated at 85° C. for 24 hours. The mixture was then cooled and purified by flash chromatography (5-25% ethyl acetate/hexane) to afford the sub-title compound as a yellow oil (17.1 g, 64%). 1H NMR (400 MHz, CDCl3) δ 0.68-1.32 (6H, m), 1.50 (21H, m), 1.92 (1H, m), 2.15 (1H, m), 2.82-3.40 (3H, m), 4.41 (1H, m), 4.68 (1H, m), 7.11 (1H, m), 7.35-7.52 (1H, m), 8.05 (1H, m) ppm.

후처리

  1. temperatureThe mixture was then cooled
  2. custompurified by flash chromatography (5-25% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-101d0f49cce24e2d9768a7e4ab24a865
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129381B2

반응 노트

불러오는 중…