L-Proline → (S)-6,7-difluoro-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

HRID 1378060노트

반응식

HRID 1378060 반응식
[F:1][C:2]1[C:7]2[C:8](=[O:13])O[C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][C:3]=1[F:14].[NH:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1C(O)=O>CN(C)C=O.C(O)(=O)C>[F:1][C:2]1[C:7]2[C:8](=[O:13])[N:15]3[CH2:22][CH2:21][CH2:20][C@H:16]3[C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][C:3]=1[F:14]

참가 물질

5

반응물 2

HCID 145742L-ProlineHCID 229144245,6-difluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

생성물 1

HCID 54321528(S)-6,7-difluoro-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione수율 82.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 28.8 g (144.6 mmol) of 5,6-difluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione and 16.7 g (144.6 mmol) of L-proline in 110 ml of dimethylformamide and 20 ml of acetic acid was stirred at 120° for 16 hours. The brown solution was evaporated and the brown residue obtained was crystallized from ethanol. There were obtained 30 g (82%) of (S)-6,7-difluoro-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione as colourless crystals of m.p. >250°.

후처리

  1. customThe brown solution was evaporated
  2. customthe brown residue obtained
  3. customwas crystallized from ethanol

출처 및 근거

ORD 기록
ord-466e9cc3f1714f048e5c4fbdc166934a
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665718

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