Cesium carbonate → HCID 67151533, compound

HRID 1805228Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:35][CH2:34][NH:33][C:32]2=[O:36])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N[C@@H]1CCCC[C@H]1N.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([N:33]3[CH2:34][CH2:35][N:31]([C:28]4[CH:27]=[CH:26][C:25]([F:24])=[CH:30][CH:29]=4)[C:32]3=[O:36])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 180 °C

Procedure

A stirred suspension of (S)-4-[(E)-2-(4-iodo-phenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (250 mg, example 3(a)), 1-(4-fluorophenyl)imidazoline-2-one (320 mg, CAS 53159-75-4), caesium carbonate (418 mg), trans-1,2-diaminocyclohexane (0.14 ml), dibenzylideneacetone (54 mg) and copper(I) triflate benzene complex (58 mg) in dioxane (3 ml) under an atmosphere of argon in a sealed tube was heated at 180° C. for 40 min under microwave irradiation. The mixture was then cooled to room temperature and was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-4-((E)-2-{4-[3-(4-fluoro-phenyl)-2-oxo-imidazolidin-1-yl]-phenyl}-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (187 mg, 67%) as an off-white solid. MS (ISP): 504.2 ([M+Na]+), 426.2 ([M+H—C4H8]+).

Workup

temperatureThe mixture was then cooled to room temperature
customwas purified by column chromatography (SiO2; gradient: heptane/EtOAc)

Sources & evidence

ORD record: ord-ef712b99e77147bd97ec27428888fb63
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354441B2

Reaction notes

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