diethyl(S)-2-(4-nitrophthalimido)glutarate → diethyl(S)-2-(4-aminophthalimido)glutarate

HRID 277697ノート

反応式

HRID 277697 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([C@@H:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8](=[O:9])[C:7]2=[CH:26][CH:27]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([C@@H:13]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8](=[O:9])[C:7]2=[CH:26][CH:27]=1

参加物

4

反応物 1

HCID 10429715diethyl(S)-2-(4-nitrophthalimido)glutarate

生成物 1

HCID 10043327diethyl(S)-2-(4-aminophthalimido)glutarate収率 88.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A suspension of diethyl (S)-2-(4-nitrophthalimido)glutarate (35.6 g, 94.1 mmol) and 10% palladium on carbon (0.5 g) (Aldrich) in ethanol (200 ml) was shaken under a hydrogen atmosphere (40-50 psi) for 26 hours. The solution was filtered through celite and concentrated in vacuo. The residue was purified by chromatography on silica gel (250 g) eluting with diethyl ether:hexane (4:1) to give diethyl (S)-2-(4-aminophthalimido)glutarate as a viscous yellow oil (29.1 g).

後処理

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (250 g)
  4. washeluting with diethyl ether:hexane (4:1)

出典と根拠

ORDレコード
ord-348e5d4e78234368bca18dc2c902195f
出典データセット
uspto-grants-2002_03
特許番号
US06358952B1

反応ノート

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