Barium hydroxide, monohydrate → (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-(2-(pent-4-enyl)-5-(trifluoromethyl)-benzylamino)butan-2-ol

HRID 501724

Reaktionsgleichung

FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:16][C@H:17]([NH:38]C(=O)OCC2C=CC=CC=2)[C@H:18]([OH:37])[CH2:19][NH:20][CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=2[CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[CH:12]=[C:13]([F:15])[CH:14]=1.O.[OH-].[Ba+2].[OH-]>COCCOC.O>[NH2:38][C@@H:17]([CH2:16][C:11]1[CH:12]=[C:13]([F:15])[CH:14]=[C:9]([F:8])[CH:10]=1)[C@H:18]([OH:37])[CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=[CH:24][C:23]=1[CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

Step AM (2): To a solution of benzyl (2S,3R)-1-(3,5-difluorophenyl)-3-hydroxy-4-(2-(pent-4-enyl)-5-(trifluoromethyl)benzylamino)butan-2-ylcarbamate trifluoroacetate salt (88 mg, 0.128 mmol) in DME (9.0 mL) and water (6.0 mL) was added barium hydroxide monohydrate (852 mg, 4.5 mmol). The reaction mixture was stirred at 110° C. in a high pressure vial for 18 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuum. The residue was purified by reverse phase chromatography to give (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-(2-(pent-4-enyl)-5-(trifluoromethyl)-benzylamino)butan-2-ol double trifluoro-acetate salt (64 mg, 74%) as a colorless oil. LC-MS (M+H)+=443.36.

Aufarbeitung

filtrationThe reaction mixture was filtered through a pad of celite
concentrationthe filtrate was concentrated in vacuum
customThe residue was purified by reverse phase chromatography

Quellen und Nachweise

ORD-Eintrag: ord-8d85c3f3950e48f08a6fc2c4cbfe9edd
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07772221B2

Verknüpfte Notizen

Wird geladen…