Neopentylamine → {(1S,2S,4S)-4-(2,2-Dimethylpropylcarbamoyl)-1-[2,2-dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazin-1-ylmethyl]-2-hydroxy-5-methylhexyl}carbamic acid t-butyl ester

HRID 1694947ノート

反応式

HRID 1694947 の反応式
[CH3:1][C:2]([CH3:6])([CH3:5])[CH2:3][NH2:4].OC1C=CC=CN=1.[C:14]([O:18][C:19](=[O:49])[NH:20][C@H:21]([C@@H:40]1[CH2:44][C@@H:43]([CH:45]([CH3:47])[CH3:46])[C:42](=[O:48])[O:41]1)[CH2:22][N:23]1[CH2:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[CH3:37])[CH2:25][C:24]1([CH3:39])[CH3:38])([CH3:17])([CH3:16])[CH3:15]>O>[C:14]([O:18][C:19](=[O:49])[NH:20][C@@H:21]([CH2:22][N:23]1[CH2:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[CH3:37])[CH2:25][C:24]1([CH3:38])[CH3:39])[C@@H:40]([OH:41])[CH2:44][C@H:43]([C:42](=[O:48])[NH:4][CH2:3][C:2]([CH3:6])([CH3:5])[CH3:1])[CH:45]([CH3:47])[CH3:46])([CH3:15])([CH3:16])[CH3:17]

参加物

5

反応物 3

HCID 79882NeopentylamineHCID 66645725{(S)-2-[2,2-Dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}carbamic acid t-butyl esterHCID 178516071HCID 178516071、化合物

生成物 1

HCID 66645581{(1S,2S,4S)-4-(2,2-Dimethylpropylcarbamoyl)-1-[2,2-dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazin-1-ylmethyl]-2-hydroxy-5-methylhexyl}carbamic acid t-butyl ester収率 75%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

0.94 ml of (2,2-dimethylpropyl)amine (8.0 mmol) and 7.6 mg of 2-hydroxypyridine (0.08 mmol) were added to 202 mg of {(S)-2-[2,2-dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}carbamic acid t-butyl ester obtained in Example (70f) (0.4 mmol), and the mixture was stirred at 70° C. for four hours. The reaction mixture was cooled and then water was added, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=20/1) to obtain 177 mg of the title compound (yield: 75%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionfollowed by extraction with ethyl acetate
  3. washThen, the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=20/1)

出典と根拠

ORDレコード
ord-c8230539d75b42739923d2014dcd4f7d
出典データセット
uspto-grants-2012_04
特許番号
US08158790B2

反応ノート

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