Water → HCID 178461142, compound

HRID 1036538Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 110 °C

Procedure

(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).

Workup

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

Sources & evidence

ORD record: ord-291e51850dd944e1a7ec0301e8817957
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Reaction notes

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