Potassium Carbonate → HCID 68675365, compound

HRID 1994068Notes

Reaction equation

HRID 1994068 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]1[N:30]=[C:31]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:32][C:33]=1[CH3:34]>CN(C=O)C>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])[CH:14]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 68676419HCID 68676419, compound

Product 1

HCID 68675365HCID 68675365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title A compound, (R)-1-[2-(3-hydroxy-phenyl)-acetyl]-pyrrolidine-2-carboxylic acid ethyl ester (1.0 g, 3.61 mmol) in 10 mL DMF is added potassium carbonate (0.60 g, 4.33 mmol) followed by 4-chloromethyl-5-methyl-2-phenyl-oxazole (0.75 g, 3.61 mmol). The mixture is stirred for 24 h at RT, and partitioned between ethyl acetate and water. The organic layer is separated and washed with brine, dried over anhydrous sodium sulfate, concentrated and purified by flash chromatography (silica gel) eluting with hexane:ethyl acetate (3:7) to give (R)-1-{2-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid ethyl ester.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatography (silica gel)
  7. washeluting with hexane:ethyl acetate (3:7)

Sources & evidence

ORD record
ord-e86c32d2783b4e9ebe9b3d5cd903491d
Source dataset
uspto-grants-2010_01
Patent number
US07652061B2

Reaction notes

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