Potassium trimethylsilanolate → 2-(3-Cyclohexyl-1,1,1-trifluoro-3-(pyrazine-2-carboxamido)propan-2-ylamino)-3,3-dimethylbutanoic acid

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Reaktionsgleichung

[CH:1]1([CH:7]([NH:23][C:24]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)=[O:25])[CH:8]([NH:13][CH:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]([O:17]C)=[O:16])[C:9]([F:12])([F:11])[F:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>O1CCCC1.C(OCC)(=O)C>[CH:1]1([CH:7]([NH:23][C:24]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)=[O:25])[CH:8]([NH:13][CH:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]([OH:17])=[O:16])[C:9]([F:11])([F:12])[F:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

The stereoisomer of methyl 2-(3-cyclohexyl-1,1,1-trifluoro-3-(pyrazine-2-carboxamido)propan-2-ylamino)-3,3-dimethylbutanoate designated as 7A1-isomer A (107 mgm), and potassium trimethylsilanolate (124 mgm, 4 eq) in tetrahydrofuran (2.5 mL) were heated to 140° C. in a microwave apparatus for 10 minutes. The reaction mixture was diluted with ethyl acetate, and washed successively with 1N hydrochloric acid, water, brine, and then dried over anhydrous sodium sulfate. Evaporation to dryness under reduced pressure gave crude 2-(3-cyclohexyl-1,1,1-trifluoro-3-(pyrazine-2-carboxamido)propan-2-ylamino)-3,3-dimethylbutanoic acid (8), designated as 8A1-isomer A.

Aufarbeitung

washwashed successively with 1N hydrochloric acid, water, brine
dry with materialdried over anhydrous sodium sulfate
customEvaporation to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-3353f46708dd445ab4e541fe5d767b74
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08106059B2

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