Cinchonidine → Cinchonidine

HRID 660080

反応式

HRID 660080 の反応式
[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[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=[CH:14][CH:13]=3)[N:5]([CH2:6][CH2:7]2)[CH2:4]1.[CH:23]1([C:29]([OH:38])([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)[C:30]([OH:32])=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[CH:23]1([C@@:29]([OH:38])([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)[C:30]([OH:32])=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[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[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=[CH:14][CH:13]=3)[N:5]([CH2:6][CH2:7]2)[CH2:4]1

参加物

5

反応物 2

HCID 101744CinchonidineHCID 13063448HCID 13063448、化合物

生成物 2

HCID 101744CinchonidineHCID 67538134(S)-Cyclohexyl-hydroxy-thiophen-2-yl-acetic acid

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
65 °C

実験手順

L-cinchonidine (30.2 g, 0.103 mol) is added to crude cyclohexyl-hydroxy-thiophen-2-yl-acetic acid (49.3 g, 103 mol assuming 50% purity of crude) followed by toluene (2.2 litres) and the mixture is heated to reflux for 70 minutes. The resulting solution is allowed to cool slowly and at 65° C., the solution is seeded. After further cooling to 40° C., the solution is placed in the fridge overnight. The resulting solid is filtered, washed with toluene and dried in vacuo. The recrystallisation process from toluene is repeated for a second time with seeding occurring at 85° C. to afford the titled compound as a salt of L-cinchonidine in 98% enantiomeric excess. The salt is added to a stirred mixture of 1M HCl (40 ml) and diethyl ether (500 ml) and stirring continues until a solution forms. The organic portion is separated, washed with brine (400 ml), dried over MgSO4 and concentrated in vacuo to give the titled compound in 98% enantiomeric excess.

後処理

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 70 minutes
  3. temperatureAfter further cooling to 40° C.
  4. customis placed in the fridge overnight
  5. filtrationThe resulting solid is filtered
  6. washwashed with toluene
  7. customdried in vacuo
  8. customoccurring at 85° C.

出典と根拠

ORDレコード
ord-6330bc72192743148861809a836e03d9
出典データセット
uspto-grants-2011_12
特許番号
US08084463B2

関連ノート

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