Ketoprofen → (S)-(-)-Ketoprofen cinchonidine

HRID 373356

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HRID 373356 반응식
[CH2:1]=[CH:2][C@@H:3]1[C@@H:8]2[CH2:9][C@@H:10]([C@H:11]([OH:22])[C:12]3[CH:13]=[CH:14][N:15]=[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.[OH:23][C:24]([CH:26]([C:28]1[CH:41]=[CH:40][CH:39]=[C:30]([C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:32])[CH:29]=1)[CH3:27])=[O:25].C(OCC)(=O)C>CO>[OH:25][C:24]([C@H:26]([C:28]1[CH:41]=[CH:40][CH:39]=[C:30]([C:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:32])[CH:29]=1)[CH3:27])=[O:23].[CH2:1]=[CH:2][C@@H:3]1[C@@H:8]2[CH2:9][C@@H:10]([C@H:11]([OH:22])[C:12]3[CH:13]=[CH:14][N:15]=[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[N:5]([CH2:6][CH2:7]2)[CH2:4]1

참가 물질

5

반응물 3

HCID 3825KetoprofenHCID 8857Ethyl AcetateHCID 101744Cinchonidine

생성물 1

HCID 131717639(S)-(-)-Ketoprofen cinchonidine수율 31%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
35 °C

실험 절차

Cinchonidine (155 g; 0.53 mol) was added to a solution of 115g (0.59 mol) of racemic ketoprofen and 2.8 L of ethyl acetate under vigorous stirring at 50°-60° C. The mixture was diluted with 280 mL of methanol, cooled to 35° C., then seeded with 98% enantiomerically pure S-salt to induce crystallization. After stirring at room temperature for 16 h and 0° C. for 5-6 h, the precipitated diastereomeric salt was filtered under vacuum, washed three times with ethyl acetate and three times with ether, and then dried under vacuum for 16 h [Yield: 127 g (or 44%); enantiomeric purity: 86% S]. One recrystallization from 1.7 L of ethyl acetate/methanol (10:1) afforded 88 g (31% yield) salt of 97% enantiomerically pure S-ketoprofen.

후처리

  1. customcrystallization
  2. stirringAfter stirring at room temperature for 16 h and 0° C. for 5-6 h
  3. filtrationthe precipitated diastereomeric salt was filtered under vacuum
  4. washwashed three times with ethyl acetate and three times with ether
  5. customdried under vacuum for 16 h [Yield: 127 g (or 44%); enantiomeric purity: 86% S]
  6. customOne recrystallization from 1.7 L of ethyl acetate/methanol (10:1)

출처 및 근거

ORD 기록
ord-59bbdc689ce24ee88b2bfe0a985a3868
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162576

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