Water → HCID 57856020, compound

HRID 1715204Notes

Reaction equation

[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:11][C:12](=[O:30])[C:13]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][CH:24]=[N:25]2)=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:10].O>CS(C)=O>[N:25]1[C:26]2[C:21](=[C:20]([C:13]3([C:12]([O:11][CH2:9][CH3:10])=[O:30])[CH2:4][CH:14]3[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:29]=[CH:28][CH:27]=2)[CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (0.93 g) was added in small portions to a stirred suspension of trimethylsulfoxonium iodide (5.12 g) in DMSO (50 mL) at room temperature. After 0.5 h, the clear reaction mixture was cooled to 0° C. and a solution of diethyl-2-(5-quinolinyl)-2-butenedioate (P24, 3.48 g) in DMSO (25 mL) was quickly added and the stirring continued for 0.5 h after which time water (30 mL) was added. The mixture was extracted twice with ether (30 mL), the organic phase was washed with saturated ammonium chloride, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel (eluting with cyclohexane-ethyl acetate from 100 to 70%) to give 3.02 g of the title compound as a slightly yellow oil.

Workup

waitthe stirring continued for 0.5 h
extractionThe mixture was extracted twice with ether (30 mL)
washthe organic phase was washed with saturated ammonium chloride
dry with materialdried over sodium sulphate
customevaporated under reduced pressure
customThe crude product was purified by flash chromatography on silica gel (eluting with cyclohexane-ethyl acetate from 100 to 70%)

Sources & evidence

ORD record: ord-d4a80d83f33442aebff28623c579a2e8
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799815B2

Reaction notes

Loading…