Potassium Carbonate → ethyl 3-{[(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-yl]methyl}phenoxyacetate

HRID 431761Notes

Reaction equation

HRID 431761 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([OH:23])[CH2:20][NH:19]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][C:32]1[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=1)[O:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>CN(C=O)C.CCOC(C)=O>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][C@@H:21]([OH:23])[CH2:20][N:19]3[CH2:31][C:32]3[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=3)[O:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11459982Ethyl 3-(bromomethyl)phenoxyacetateHCID 11460944(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-4-ol

Product 1

HCID 11156247ethyl 3-{[(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-yl]methyl}phenoxyacetateYield 96.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (2R, 4R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-4-ol (229 mg) and potassium carbonate (155 mg) in DMF (5 mL) was added ethyl 3-(bromomethyl)phenoxyacetate (245 mg) at 5° C. and stirred at the same temperature for 30 minutes then at room temperature for 16 hours. The reaction mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc, 1:2) to give ethyl 3-{[(2R, 4R)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidin-1-yl]methyl}phenoxyacetate (359.7 mg).

Workup

  1. waitat room temperature for 16 hours
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane-EtOAc, 1:2)

Sources & evidence

ORD record
ord-bb7f67299e8f469abe33e68ee55ec233
Source dataset
uspto-grants-2003_12
Patent number
US06660759B1

Reaction notes

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