3-(2-Cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester → 3-(2-Cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid

HRID 1181101Notes

Reaction equation

HRID 1181101 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][C:8]=1[C:35]#[N:36])C>CCO.[OH-].[Na+]>[C:35]([C:8]1[CH:9]=[C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])[CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][C:4]([OH:37])=[O:3])#[N:36]

Participants

4

Reactant 1

HCID 692321723-(2-Cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester

Product 1

HCID 102053193-(2-Cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-(3-ethoxy-but-3-enyl)-5-hydroxy-benzonitrile (220 mg, 1.00 mmol), toluene-4-sulfonic acid 2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethyl ester (450 mg, 1.00 mmol; Preparation 6), and CsCO3 (978 mg, 3.00 mmol) in DMF (10 mL) was stirred overnight at 60° C. under an N2. The mixture was cooled, diluted with EtOAc (20 mL) and washed with brine (20 mL). The organic layer was dried (Na2SO4) and concentrated. The product mixture was purified by radial chromatography (10-70% EtOAc/hexanes) to give 3-(2-cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester (201 mg). A solution of this ester in EtOH (10 mL) and 5N NaOH (10 mL) was heated at 70° C. overnight, concentrated, acidified with 1N HCl, and extracted with EtOAc. The organic layer dried (Na2SO4) and concentrated to give the title compound (192 mg); MS [ES] m/z 469 (M+1).

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-980ecccf7a7340f988e6fc53a7dc7f46
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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