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

HRID 54035

反応式

HRID 54035 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 131719976(S)-ibuprofen N-octyl-D-glucamine salt収率 83.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

Racemic ibuprofen (18.03 g, 87.4 mmol), N-octyl-D-glucamine (12.12 g, 41.3 mmol), triethylamine (4.4 g, 43.5 mmol), water (0.5 mL), and toluene (150 mL) were heated to 80° C., forming a clear solution. The solution was cooled to 25° C. over 2 1/2 hours, then cooled in an ice bath to 15° C. The resulting crystalline precipitate was recovered by filtration, washed with toluene, and dried to give (S)-ibuprofen N-octyl-D-glucamine salt (17.2 g, 78.8% yield, 94.8% ee).

後処理

  1. customforming a clear solution
  2. temperaturecooled in an ice bath to 15° C
  3. filtrationThe resulting crystalline precipitate was recovered by filtration
  4. washwashed with toluene
  5. customdried

出典と根拠

ORDレコード
ord-35ee6ae184d34e9e99eed5912c2385b9
出典データセット
uspto-grants-1997_04
特許番号
US05621140

関連ノート

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