Hydrochloric Acid → (2S)-2-(((tert-butoxy)carbonyl)amino)-4-cyclohexylbutanoic acid

HRID 383162

Reaktionsgleichung

[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.O1CCOCC1.[OH-].[Na+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(Cl)Cl.[Pt].Cl.C1COCC1.O>[C:4]([O:3][C:1]([NH:8][C@@H:9]([CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[C:18]([OH:20])=[O:19])=[O:2])([CH3:7])([CH3:5])[CH3:6]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a solution of Boc-homophenylalanine (3.00 g, 10.8 mmol) in CH2Cl2 at room temperature was added a solution of 4N HCl in dioxane (20 mL, 80 mmol), and mixture stirred overnight. Solvents concentrated, and white powder that resulted was reduced under high pressure (4 atm. H2) using platinum/HCl. The white solid that resulted from the reduction was mixed with aqueous 4N NaOH (30 mL), water (30 mL), and THF (50 mL) at room temperature, and to this was added di-t-butyl dicarbonate (3.5 g, 16 mmol). Reaction heated at 70° C. overnight. Reaction cooled to 0° C., and an aqueous solution of 3N HCl added until the pH reached 6. Product extracted out with CHCl3, and extracts dried with Na2SO4, filtered, and concentrated in vacuo to produce a white solid (3.24 g, 106%). m/e (DCI) 286 (MH+)

Aufarbeitung

concentrationSolvents concentrated
customwhite powder that resulted
customThe white solid that resulted from the reduction
customReaction
customReaction
temperaturecooled to 0° C.
extractionProduct extracted out with CHCl3, and extracts
dry with materialdried with Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-9c42513025ff49dba74ab9f6c43a8dd9
Quelldatensatz: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06310095B1

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