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 1948498노트

반응식

[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

참가 물질

반응물 2

HCID 204431481,4-Dioxane hydrochloride

HCID 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

생성물 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 acid수율 99.2%

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록: ord-1b1927f4f70c488aa4adb57f799e613d
출처 데이터셋: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08399451B2

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