Isobutylamine → {(1S,2S,4R)-4-(Isobutylcarbamoyl)-1-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-ylmethyl]-2-hydroxyhexyl}carbamic acid t-butyl ester

HRID 1694999ノート

反応式

HRID 1694999 の反応式
OC1C=CC=CN=1.[C:8]([O:12][C:13](=[O:41])[NH:14][C@H:15]([C@@H:33]1[CH2:37][C@@H:36]([CH2:38][CH3:39])[C:35](=[O:40])[O:34]1)[CH2:16][N:17]1[CH2:22][C:21](=[O:23])[N:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH2:19][C:18]1([CH3:32])[CH3:31])([CH3:11])([CH3:10])[CH3:9].[CH2:42]([NH2:46])[CH:43]([CH3:45])[CH3:44]>O>[C:8]([O:12][C:13](=[O:41])[NH:14][C@@H:15]([CH2:16][N:17]1[CH2:22][C:21](=[O:23])[N:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH2:19][C:18]1([CH3:32])[CH3:31])[C@@H:33]([OH:34])[CH2:37][C@H:36]([C:35](=[O:40])[NH:46][CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:38][CH3:39])([CH3:9])([CH3:10])[CH3:11]

参加物

5

反応物 3

HCID 6558IsobutylamineHCID 66645434{(S)-2-[4-(2-Chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl}carbamic acid t-butyl esterHCID 178516071HCID 178516071、化合物

生成物 1

HCID 66645671{(1S,2S,4R)-4-(Isobutylcarbamoyl)-1-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-ylmethyl]-2-hydroxyhexyl}carbamic acid t-butyl ester収率 92.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

24 mg of 2-hydroxypyridine (0.26 mmol) was added to a solution of 250 mg of {(S)-2-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl}carbamic acid t-butyl ester obtained in Example (106i) (0.51 mmol) in isobutylamine (0.99 ml) (10.2 mmol), and the mixture was stirred at 80° C. for two hours. The reaction mixture was cooled and then water was added, followed by extraction with methylene chloride. Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/acetone=3/1-2/1) to obtain 267 mg of the title compound (yield: 92%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution solvent:methylene chloride/acetone=3/1-2/1)

出典と根拠

ORDレコード
ord-ffd31229189e4d02b86a5a1ee4351de4
出典データセット
uspto-grants-2012_04
特許番号
US08158790B2

反応ノート

読み込み中…