Water → HCID 178461142, Verbindung

HRID 2389197Notizen

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[C@H:30]1[CH2:35][CH2:34][C@@H:33]([C:36]([F:39])([F:38])[CH3:37])[CH2:32][CH2:31]1)(=O)=O.O>CC(O)(C)C.CC(=O)CC>[F:38][C:36]([C@H:33]1[CH2:34][CH2:35][C@H:30]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C@:12]2([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[CH:6]=[CH:5]3)[CH2:31][CH2:32]1)([F:39])[CH3:37]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

(R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (121 mg, 0.5 mmol, 0.9 eq.) and cesium carbonate (407 mg, 1.25 mmol, 2.5 eq.) were dissolved in t-BuOH/2-butanone (10 mL/5 mL). The mixture was stirred at 110° C. for 10 min, then cis-4-(1,1-difluoroethyl)cyclohexyl methanesulfonate (145 mg, 0.6 mmol, 1.1 eq.) was added to the mixture and the mixture was stirred at 110° C. for 15 h. Water was added to the mixture and the mixture was extracted with EtOAc. The organic layer was concentrated and purified by is silica gel column chromatography using petroleum ether/ethyl acetate (1/1) as eluent to give product (203 mg, 58%) as a slight yellow solid. EDI-MS (M+1): 390.1. 1H NMR (400 MHz, CDCl3) δ 7.75-7.72 (m, 3H), 7.42 (dd, 1H), 7.16-7.14 (m, 2H), 6.14 (s, 1H), 4.42 (s, 2H), 4.34-4.30 (m, 1H), 2.31-2.29 (m, 2H), 2.04-2.01 (m, 2H), 1.84 (s, 3H), 1.64-1.22 (m, 8H).

Aufarbeitung

stirringthe mixture was stirred at 110° C. for 15 h
extractionthe mixture was extracted with EtOAc
concentrationThe organic layer was concentrated
custompurified

Quellen und Nachweise

ORD-Eintrag: ord-79d7d474996649d2a5bb9b747a920181
Quelldatensatz: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08269043B2

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