Nitrogen → (S)-[1-(hydroxy-oxazolo[4,5-b]pyridin-2-yl-methyl)-propyl]-carbamic acid tert-butyl ester

HRID 1796138

Reaktionsgleichung

[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.[Li]CCCC.N#N.CCOCC.[C:22]([O:26][C:27](=[O:34])[NH:28][C@H:29]([CH:32]=[O:33])[CH2:30][CH3:31])([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([O:26][C:27](=[O:34])[NH:28][C@H:29]([CH:32]([OH:33])[C:2]1[O:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:30][CH3:31])([CH3:23])([CH3:24])[CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: -45 °C

Versuchsvorschrift

Alternative procedure: To a stirred solution of the oxazolo[4,5-b]pyridine (12 g, 100 mmol) in THF (300 ml) was added n-BuLi (1.6M solution in 62.5 ml of hexane) drop wise under N2 at −78° C. After 1 hour, MgBr.Et2O (25.8 g, 100 mmol) was added and the reaction mixture was allowed to warm to −45° C. for 1 hour before being treated with (S)-(1-formyl-propyl)-carbamic acid tert-butyl ester (11.46 g, 60 mmol) in THF (50 ml). The reaction mixture was stirred for 1 hour, quenched with saturated NH4Cl, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4 and concentrated. The residue was purified by silica gel column chromatography to yield (S)-[1-(hydroxy-oxazolo[4,5-b]pyridin-2-yl-methyl)-propyl]-carbamic acid tert-butyl ester (14.1 g).

Aufarbeitung

customquenched with saturated NH4Cl
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried with MgSO4
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-139c683a82b747e89d1d36fb447a7696
Quelldatensatz: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07030116B2

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