Cesium carbonate → HCID 18930691, compound

HRID 968767Notes

Reaction equation

HRID 968767 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[OH:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:7]([O:6][C:5]([NH:4][CH2:3][CH2:2][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:11])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 88068Methyl 3-HydroxybenzoateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 18930691HCID 18930691, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 2-bromoethylcarbamate (5 g) and methyl 3-hydroxybenzoate (3.4 g) in dimethylformamide (60 ml) was added caesium carbonate (14.5 g) and the reaction stirred for 12 hours before partitioning between water and ethyl acetate. The organic layer was separated, dried with MgSO4 and the solvent removed by evaporation. Purification by flash chromatography (ethyl acetate:isohexane 92.5:7.5) gave the sub-title product as a colourless oil (3 g).

Workup

  1. custombefore partitioning between water and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. customthe solvent removed by evaporation
  5. customPurification by flash chromatography (ethyl acetate:isohexane 92.5:7.5)

Sources & evidence

ORD record
ord-3ad07ba5b2b64bd0b34120d21fd4e6e6
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

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