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 1948498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948498
[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

Komponenten

3

Edukt 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

Produkt 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 acidAusbeute 99,2 %

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1b1927f4f70c488aa4adb57f799e613d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399451B2

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