Water → (2R)-2-amino-2-ethoxycarbonylsuccinimide

HRID 1661870ノート

反応式

HRID 1661870 の反応式
C(OC([NH:11][C@:12]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16](=[O:18])[NH:15][C:13]1=[O:14])=O)C1C=CC=CC=1.O.[H][H]>C(O)C.[Pd]>[NH2:11][C@:12]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16](=[O:18])[NH:15][C:13]1=[O:14]

参加物

6

反応物 3

HCID 962WaterHCID 9944916(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 10679104(2R)-2-amino-2-ethoxycarbonylsuccinimide収率 86.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
35 °C

実験手順

(2R)-2-Benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide (24.4 g, 76.2 mmol) in ethanol (73.2 ml) was heated at 60° C. to be dissolved and 5% Pd—C (2.71 g) and water (2.17 g) were added at 30-40° C. of inner temperature. After the atmosphere was substituted with nitrogen gas, hydrogen gas was introduced and the mixture was stirred at 30-40° C. for about 33 hours. When completion of the reaction was confirmed by HPLC, the reaction solution was filtered, the insoluble materials were washed with sprayed ethanol (20 ml×2) and the filtrate was concentrated. The resulting crystals were recrystallized from ethanol (24.4 ml) and the precipitated crystals were filtered, washed with sprayed ethanol (15 ml) and dried in vacuo at room temperature to give (2R)-2-amino-2-ethoxycarbonylsuccinimide (12.3 g). Yield 86.7%, HPLC 99.7%, Optical purity 100% e.e.

後処理

  1. dissolutionto be dissolved
  2. additionwas introduced
  3. filtrationthe reaction solution was filtered
  4. washthe insoluble materials were washed with sprayed ethanol (20 ml×2)
  5. concentrationthe filtrate was concentrated
  6. customThe resulting crystals were recrystallized from ethanol (24.4 ml)
  7. filtrationthe precipitated crystals were filtered
  8. washwashed with sprayed ethanol (15 ml)
  9. customdried in vacuo at room temperature

出典と根拠

ORDレコード
ord-7f4e97dd0b1a45fa8cd8f98b80fc46a4
出典データセット
uspto-grants-2011_10
特許番号
US08030486B2

反応ノート

読み込み中…