benzyl (2S,3R)-4-((R)-2-(allyloxy)-1-phenylethylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate → (2R,3S)-1-((R)-2-(allyloxy)-1-phenylethylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol

HRID 501682노트

반응식

HRID 501682 반응식
[CH2:1]([O:4][CH2:5][C@H:6]([NH:13][CH2:14][C@@H:15]([OH:37])[C@@H:16]([NH:26]C(=O)OCC1C=CC=CC=1)[CH2:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:2]=[CH2:3]>COCCOC.O>[CH2:1]([O:4][CH2:5][C@H:6]([NH:13][CH2:14][C@@H:15]([OH:37])[C@@H:16]([NH2:26])[CH2:17][C:18]1[CH:19]=[C:20]([F:25])[CH:21]=[C:22]([F:24])[CH:23]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:2]=[CH2:3]

참가 물질

3

반응물 1

HCID 86622319benzyl (2S,3R)-4-((R)-2-(allyloxy)-1-phenylethylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate

생성물 1

HCID 59423789(2R,3S)-1-((R)-2-(allyloxy)-1-phenylethylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol수율 68%

시약·촉매·용매 1

HCID 18180031Water 1,2-dimethoxyethane용매

반응 조건

온도
110 °C

실험 절차

Step Q (5): A mixture of benzyl (2S,3R)-4-((R)-2-(allyloxy)-1-phenylethylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate (1.1 g, 2.15 mmol) from step Q (4), Ba(OH)2.H2O (1.23 g, 6.47 mmol), and DME/H2O (12 mL/8 mL) was heated at 110° C. in a sealed tube. After 18 h, the vessel was cooled to rt and the precipitate was removed by filtration. The vessel and filtercake were rinsed with fresh DME and the combined filtrates were concentrated in vacuo. The crude product was purified by silica gel chromatography to give 550 mg (68% yield) of the title compound as a yellow viscous oil. LC-MS (M+H)+=377.4; 1H NMR (300 MHz, CDCl3) δ ppm 2.46-3.01 (m, 3H) 3.13-3.72 (m, 7H) 3.89-4.04 (m, 2H) 5.10-5.28 (m, 2H) 5.77-5.96 (m, 1H) 6.52-6.78 (m, 3H) 7.24-7.41 (m, 4H).

후처리

  1. temperaturethe vessel was cooled to rt
  2. customthe precipitate was removed by filtration
  3. washThe vessel and filtercake were rinsed with fresh DME
  4. concentrationthe combined filtrates were concentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-21e9ea14c1034daea4d27b9f9100b4e1
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772221B2

반응 노트

불러오는 중…