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

HRID 54036

반응식

HRID 54036 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].[CH2:16]([NH:24][CH2:25][C@@H:26]([C@H:28]([C@@H:30]([C@@H:32]([CH2:34][OH:35])[OH:33])[OH:31])[OH:29])[OH:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH2:16]([NH:24][CH2:25][C@@H:26]([C@H:28]([C@@H:30]([C@@H:32]([CH2:34][OH:35])[OH:33])[OH:31])[OH:29])[OH:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[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

6

반응물 4

HCID 962WaterHCID 3672Ibuprofen, (+-)-HCID 8471TriethylamineHCID 900641-Deoxy-1-(octylamino)-D-glucitol

생성물 1

HCID 131719976(S)-ibuprofen N-octyl-D-glucamine salt수율 87.2%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
25 °C

실험 절차

Racemic ibuprofen (18.03 g, 87.4 mmol), N-octyl-D-glucamine (12.12 g, 41.3 mmol), triethylamine (8.6 g, 88 mmol), water (0.5 mL), and toluene (150 mL) were heated to 80° C., forming a clear solution. The solution was cooled slowly to 25° C. The resulting crystalline precipitate was recovered by filtration, washed with toluene, and dried to give (S)-ibuprofen N-octyl-D-glucamine salt (18.0 g, 82.4% yield, 86.4% ee).

후처리

  1. customforming a clear solution
  2. filtrationThe resulting crystalline precipitate was recovered by filtration
  3. washwashed with toluene
  4. customdried

출처 및 근거

ORD 기록
ord-0c658f9fdb5444a4a40ce754718f35a8
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621140

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