1,4-Dioxane hydrochloride → 2-((3R)-1-(2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetic acid

HRID 1948498ノート

反応式

HRID 1948498 の反応式
[Si]([O:8][C@@H:9]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:33]=[C:32]([C:34]3[O:38][N:37]=[C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:35]=3[C:45]([F:48])([F:47])[F:46])[O:31][N:30]=2)=[CH:25][CH:24]=1)[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:12]1)(C(C)(C)C)(C)C.Cl.O1CCOCC1>>[OH:8][CH:9]([C:23]1[CH:24]=[CH:25][C:26]([C:29]2[N:33]=[C:32]([C:34]3[O:38][N:37]=[C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:35]=3[C:45]([F:48])([F:47])[F:46])[O:31][N:30]=2)=[CH:27][CH:28]=1)[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][C:18]([OH:20])=[O:19])[CH2:12]1

参加物

3

反応物 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58374082Ethyl 2-((R)-1-((S)-2-(tert-butyldimethylsilyloxy)-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetate

生成物 1

HCID 669554722-((3R)-1-(2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetic acid収率 99.2%

実験手順

Ethyl 2-((R)-1-((S)-2-(tert-butyldimethylsilyloxy)-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetate (840 mg, 1.227 mmol) was heated in 1:1 6N HCl/dioxane at 50° C. overnight. The product was concentrated in vacuo and freeze dried from MeCN/water to yield 660 mg of 2-((3R)-1-(2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetic acid. Characterization of product by 1H NMR and chiral HPLC matched Example 18 prepared in previous synthesis.

後処理

  1. concentrationThe product was concentrated in vacuo and freeze
  2. dry with materialdried from MeCN/water

出典と根拠

ORDレコード
ord-1b1927f4f70c488aa4adb57f799e613d
出典データセット
uspto-grants-2013_03
特許番号
US08399451B2

反応ノート

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