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 501682ノート

反応式

HRID 501682 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-21e9ea14c1034daea4d27b9f9100b4e1
出典データセット
uspto-grants-2010_08
特許番号
US07772221B2

反応ノート

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