Potassium Carbonate → HCID 86605610, compound

HRID 1994072Notes

Reaction equation

HRID 1994072 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1)=[O:12])=[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.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][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:15]=1)=[O:12])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 86605611HCID 86605611, compound

Product 1

HCID 86605610HCID 86605610, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the title C compound, 1-(3-hydroxy-phenylsulfanylcarbonyl)-pyrrolidine-2-carboxylic acid ethyl ester (1.1 g, 3.73 mmol) and potassium carbonate (0.78 g, 5.59 mmol) in DMF (25 mL) is added 4-chloromethyl-5-methyl-2-phenyl-oxazole (0.78 g, 3.73 mmol) at RT. The reaction mixture is stirred for 16 h. The stirring is continued for another 3 h at 40° C. The reaction mixture is cooled to RT, diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated at reduced pressure. The crude product is purified on a Biotage 40M column using 25% ethyl acetate in hexane to yield (R)-1-[3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenylsulfanylcarbonyl]-pyrrolidine-2-carboxylic acid ethyl ester as a clear, heavy oil.

Workup

  1. waitThe stirring is continued for another 3 h at 40° C
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customThe crude product is purified on a Biotage 40M column

Sources & evidence

ORD record
ord-7914b3e9d86c428c8e656a1f2bab41c6
Source dataset
uspto-grants-2010_01
Patent number
US07652061B2

Reaction notes

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