HCID 11608784、化合物 → (R)-3-((E)-2-(pyrrolidin-3-yl)vinyl)-5-(tetrahydropyran-4-yloxy)pyridine di-p-toluoyl-D-tartrate

HRID 472896

反応式

HRID 472896 の反応式
[NH:1]1[CH2:5][CH2:4][C@H:3](/[CH:6]=[CH:7]/[C:8]2[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:13]=2)[CH2:2]1.[C:21]1([CH3:48])[CH:26]=[CH:25][C:24]([C:27]([C@:29]([C:45]([OH:47])=[O:46])([OH:44])[C@:30]([C:35]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)=[O:36])([OH:34])[C:31]([OH:33])=[O:32])=[O:28])=[CH:23][CH:22]=1>C(O)C>[C:21]1([CH3:48])[CH:26]=[CH:25][C:24]([C:27]([C@:29]([C:45]([OH:47])=[O:46])([OH:44])[C@:30]([C:35]([C:37]2[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=2)=[O:36])([OH:34])[C:31]([OH:33])=[O:32])=[O:28])=[CH:23][CH:22]=1.[NH:1]1[CH2:5][CH2:4][C@H:3](/[CH:6]=[CH:7]/[C:8]2[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:13]=2)[CH2:2]1

参加物

4

反応物 2

HCID 11608784HCID 11608784、化合物HCID 22860073(2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid

生成物 1

HCID 131729628(R)-3-((E)-2-(pyrrolidin-3-yl)vinyl)-5-(tetrahydropyran-4-yloxy)pyridine di-p-toluoyl-D-tartrate収率 72.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
27.5 °C

実験手順

To a stirred solution of (R)-3-((E)-2-(pyrrolidin-3-yl)vinyl)-5-(tetrahydropyran-4-yloxy)pyridine (4.0 g, 15 mmol) in ethanol (12.5 mL) solution, heated to 60° C., was added solid di-p-toluoyl-D-tartaric acid (5.3 g, 14 mmol). The solution was held at 60° C. for 2-3 min to ensure complete dissolution of the solids, then the heat source was removed and the solution was cooled to 25-30° C. over 60 min. The resulting suspension was held at 25-30° C. for 30 min, and then filtered to collect the solids. The solids were washed with ethanol (2×20 mL), air dried for 30 min, then dried in a vacuum oven under reduced pressure at 50° C., until a constant weight was established, to give (R)-3-((E)-2-(pyrrolidin-3-yl)vinyl)-5-(tetrahydropyran-4-yloxy)pyridine di-p-toluoyl-D-tartrate as an off-white solid (6.7 g, 72%). NNNMR analysis indicated a 1:1 salt stoichiometry. 1H-NMR (DMSO-d6, 400 MHz) δ 8.18 (s, 1 H), 8.15 (s, 1 H), 7.86 (d, 4 H), 7.47 (s, 1 H), 7.32 (d, 4 H), 6.43 (d, 1 H), 6.36 (m, 1 H), 5.67 (s, 2 H), 4.69 (m, 1 H), 3.85 (m, 2 H), 3.49 (m, 2 H), 3.25 (m, 2 H), 3.10 (m, 1 H), 2.88 (m, 2 H), 2.39 (s, 6 H), 1.98 (m, 3 H), 1.60 (m, 3 H).

後処理

  1. dissolutiondissolution of the solids
  2. customthe heat source was removed
  3. waitThe resulting suspension was held at 25-30° C. for 30 min
  4. filtrationfiltered
  5. customto collect the solids
  6. washThe solids were washed with ethanol (2×20 mL), air
  7. customdried for 30 min
  8. customdried in a vacuum oven under reduced pressure at 50° C., until a constant weight

出典と根拠

ORDレコード
ord-d5d51352eb8c463ba6e2c4e4a574c9c4
出典データセット
uspto-grants-2014_01
特許番号
US08633227B2

関連ノート

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