Water → (S)-ibuprofen N-octyl-D-glucamine salt

HRID 54032

반응식

HRID 54032 반응식
[OH:1][C:2]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=[O:3].O.[CH2:17]([NH:25][CH2:26][C@@H:27]([C@H:29]([C@@H:31]([C@@H:33]([CH2:35][OH:36])[OH:34])[OH:32])[OH:30])[OH:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1(C)C=CC=CC=1>[CH2:17]([NH:25][CH2:26][C@@H:27]([C@H:29]([C@@H:31]([C@@H:33]([CH2:35][OH:36])[OH:34])[OH:32])[OH:30])[OH:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH:3][C:2]([C@H:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][CH:11]([CH3:12])[CH3:13])=[CH:14][CH:15]=1)[CH3:5])=[O:1]

참가 물질

5

반응물 3

HCID 962WaterHCID 3672Ibuprofen, (+-)-HCID 900641-Deoxy-1-(octylamino)-D-glucitol

생성물 1

HCID 131719976(S)-ibuprofen N-octyl-D-glucamine salt수율 73.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
75 °C

실험 절차

Initial resolution. Racemic ibuprofen (18 g, 87 mmol) was dissolved in toluene (150 mL), and water (0.5 mL) and N-octyl-D-glucamine (12.12 g, 41 mmol) were added to the solution. The mixture was heated slowly to 75° C., forming a clear solution, and the solution then cooled to 20° C. over 3 hours. The resulting precipitate was recovered by filtration, washed with toluene (50 mL), and dried to give (S)-ibuprofen N-octyl-D-glucamine salt (14.75 g, 30 mmol, MR=136.5°~137° C., [α]D =-11.2° (c=0.1, MeOH), 99% ee). The toluene liquors were saved for racemization and recycle of the contained (R)-ibuprofen.

후처리

  1. customforming a clear solution
  2. temperaturethe solution then cooled to 20° C. over 3 hours
  3. filtrationThe resulting precipitate was recovered by filtration
  4. washwashed with toluene (50 mL)
  5. customdried

출처 및 근거

ORD 기록
ord-06b5d336a6de4a01959f576e6454bede
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621140

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