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

HRID 1661870노트

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HRID 1661870 반응식
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]

참가 물질

6

반응물 3

HCID 962WaterHCID 9944916(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 10679104(2R)-2-amino-2-ethoxycarbonylsuccinimide수율 86.7%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
35 °C

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-7f4e97dd0b1a45fa8cd8f98b80fc46a4
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030486B2

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