Water → {(1S,2S,4R)-4-(2,2-Dimethylpropylcarbamoyl)-1-[2,2-dimethyl-4-(2-methylphenyl)-5-oxopiperazin-1-ylmethyl]-2-hydroxypentyl}carbamic acid t-butyl ester

HRID 1694965ノート

反応式

HRID 1694965 の反応式
OC1C=CC=CN=1.[C:8]([O:12][C:13](=[O:40])[NH:14][C@H:15]([C@@H:33]1[CH2:37][C@@H:36]([CH3:38])[C:35](=[O:39])[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[CH3:30])[CH2:19][C:18]1([CH3:32])[CH3:31])([CH3:11])([CH3:10])[CH3:9].O.[CH3:42][C:43]([CH3:47])([CH3:46])[CH2:44][NH2:45]>>[C:8]([O:12][C:13](=[O:40])[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[CH3:30])[CH2:19][C:18]1([CH3:32])[CH3:31])[C@@H:33]([OH:34])[CH2:37][C@H:36]([C:35](=[O:39])[NH:45][CH2:44][C:43]([CH3:47])([CH3:46])[CH3:42])[CH3:38])([CH3:11])([CH3:9])[CH3:10]

参加物

5

反応物 4

HCID 962WaterHCID 79882NeopentylamineHCID 66645428{(S)-2-[2,2-Dimethyl-4-(2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}carbamic acid t-butyl esterHCID 178516071HCID 178516071、化合物

生成物 1

HCID 66645452{(1S,2S,4R)-4-(2,2-Dimethylpropylcarbamoyl)-1-[2,2-dimethyl-4-(2-methylphenyl)-5-oxopiperazin-1-ylmethyl]-2-hydroxypentyl}carbamic acid t-butyl ester収率 85%

反応条件

温度
80 °C

実験手順

6.8 mg of 2-hydroxypyridine (0.072 mmol) was added to a solution of 165 mg of {(S)-2-[2,2-dimethyl-4-(2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}carbamic acid t-butyl ester obtained in Example (85b) (0.36 mmol) in (2,2-dimethylpropyl)amine (1.5 ml), and the mixture was stirred at 80° C. for 2.5 hours. The reaction mixture was cooled and then water was added, followed by extraction with ethyl acetate. 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/methanol=20/1) to obtain 167 mg of the title compound (yield: 85%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionfollowed by extraction with ethyl acetate
  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/methanol=20/1)

出典と根拠

ORDレコード
ord-ef15732eb18d4c8fa211ca77b1d52ccc
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…