Cesium carbonate → HCID 67509414, compound

HRID 1770731Notes

Reaction equation

HRID 1770731 reaction equation
[SH:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:16]([CH:18]1[CH2:20][O:19]1)=[CH2:17]>CN(C)C=O>[OH:19][CH:18]([CH:16]=[CH2:17])[CH2:20][S:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13586VinyloxiraneHCID 86665538HCID 86665538, compound

Product 1

HCID 67509414HCID 67509414, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(mercaptomethyl)-4-methyloxazolidin-2-one (1.79 g, 12.2 mmol) in N,N-dimethylformamide (20 ml) was added cesium carbonate (520 mg, 1.60 mmol) and 2-vinyloxirane (2.34 g, 33.4 mmol). The solution was heated to 60° C. for 14 hours, cooled to room temperature, concentrated in vacuo, and purified by flash chromatography (30% to 100% ethyl acetate in hexanes) to afford the title compound as a clear oil (quantitative). LRMS (ESI/APCI) m/z 218 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography (30% to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-09eb90f32e8d49f0bbc0f5be150d2305
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

Loading…