N-(Benzyloxycarbonyl)aspartic acid → (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

HRID 356826

반응식

HRID 356826 반응식
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C(OC(=O)C)(=O)C>[CH2:4]([O:3][C:1]([NH:11][C@@H:12]1[C:17](=[O:18])[O:19][C:14](=[O:16])[CH2:13]1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

참가 물질

3

반응물 1

HCID 2723942N-(Benzyloxycarbonyl)aspartic acid

생성물 1

HCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

반응 조건

온도
75 °C

실험 절차

The above illustrated starting compound which is commercially available N-CBZ aspartic acid (205.7 g, 0.77 mol) was added to acetic anhydride (300 ml). This mixture was stirred at 75° C. for 4 hours. The excess acetic anhydride and acetic acid byproduct were distilled from the mixture under reduced pressure and the residue was recrystallised from hot dichloromethane. The product was collected by filtration, washed with hexane and dried at ambient temperature under reduced pressure to give a white fluffy solid.

후처리

  1. distillationThe excess acetic anhydride and acetic acid byproduct were distilled from the mixture under reduced pressure
  2. customthe residue was recrystallised from hot dichloromethane
  3. filtrationThe product was collected by filtration
  4. washwashed with hexane
  5. customdried at ambient temperature under reduced pressure
  6. customto give a white fluffy solid

출처 및 근거

ORD 기록
ord-f220232a1ce74980bd2c13304127a203
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840667

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