Acetic Acid → tert-Butyl [(3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl]carbamate

HRID 1511452

Reaktionsgleichung

[CH:1]1([N+:4]#[C-:5])[CH2:3][CH2:2]1.[O:6]=[CH:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH2:10][CH3:11].C(O)(=[O:22])C>C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([NH:4][C:5](=[O:22])[CH:7]([OH:6])[C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH2:10][CH3:11])[CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of cyclopropylisonitrile (1.91 g, 28.5 mmol), (S)-tert-butyl 1-oxopentan-2-ylcarbamate (3.8 g, 19 mmol) in methylene chloride (100 mL) was added acetic acid (2.28 g, 38 mmol) at 0° C. After the addition was complete the reaction mixture was allowed to warm to 25° C. and stirred for 6 hours. The reaction mixture was diluted with ethyl acetate (200 mL), then washed with a saturated solution of sodium bicarbonate and brine (30 mL) and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the crude product was crystallized from 50 mL of ethyl acetate and hexane(v/v=1/1) to give tert-butyl (3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamate (4.8 g) as a white solid.

Aufarbeitung

additionAfter the addition
washwashed with a saturated solution of sodium bicarbonate and brine (30 mL)
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customthe crude product was crystallized from 50 mL of ethyl acetate and hexane(v/v=1/1)

Quellen und Nachweise

ORD-Eintrag: ord-8b8843b3851a4d78b8d746d1c3319784
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08211897B2

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