Tetrahydrofuran → (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

HRID 2037500Notizen

Reaktionsgleichung

[C:1]([NH:4][NH:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]([N:15]2[CH2:20][CH2:19][C@:18]([CH2:28][CH:29]=[CH2:30])([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[O:17][C:16]2=[O:31])[CH3:14])=[CH:9][CH:8]=1)(=O)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.C1COCC1>CCOC(C)=O>[CH2:28]([C@@:18]1([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:17][C:16](=[O:31])[N:15]([C@H:13]([C:10]2[CH:9]=[CH:8][C:7]([C:6]3[O:32][C:1]([CH3:2])=[N:4][N:5]=3)=[CH:12][CH:11]=2)[CH3:14])[CH2:20][CH2:19]1)[CH:29]=[CH2:30]

Komponenten

Reaktionsbedingungen

Temperatur: 180 °C

Versuchsvorschrift

Crude N′-acetyl-4-((S)-1-((R)-6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)ethyl)benzohydrazide (5 mg, 0.0114 mmol) was mixed with Burgess reagent (˜4 mg, excess), dry THF (1 mL) and put into Microwave Oven, heated to 180° C. for 10 min. at 100 W. LC-MS found reaction completed. The mixture was diluted with EtOAc (8 mL), washed with water (2×3 mL), concentrated and purified by prep HPLC to afford (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one (1.4 mg, 29%). LC-MS Method 1 tR=1.61, min, m/z=422; 1H NMR (CDCl3) 7.77 (d, 2H), 7.26 (m, 3H), 7.01 (m, 3H), 5.70 (m, 2H), 5.07 (dd, 2H), 2.98 (m, 1H), 2.62 (s, 3H), 1.55 (d, 3H).

Aufarbeitung

customreaction
washwashed with water (2×3 mL)
concentrationconcentrated
custompurified by prep HPLC

Quellen und Nachweise

ORD-Eintrag: ord-bd263801f2ea45d98128632d477e2d71
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08575156B2

Notizen zur Reaktion

Wird geladen…