Hydrochloric Acid → HCID 58765804, compound

HRID 860671Notes

Reaction equation

HRID 860671 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH:31]([CH3:33])[CH3:32])[CH3:14])=[CH:8][C:7]=1[CH3:34].[OH-].[Na+].Cl>CO.C1COCC1>[CH:31]([C:16]1[N:17]=[C:18]([C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]([F:29])([F:30])[F:28])=[CH:24][CH:25]=2)[O:19][C:15]=1[CH:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[C:7]([CH3:34])[CH:8]=1)[CH3:14])([CH3:32])[CH3:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69589326HCID 69589326, compound

Product 1

HCID 58765804HCID 58765804, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-{1-[4-Isopropyl-2-(4-trifluoromethoxy-phenyl)-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester in MeOH (1.0 mL) and THF (0.5 mL) is treated with NaOH (1.5 mL, 2.0 M) and stirred at room temperature for 2 hours. The mixture is neutralized to pH=6 with HCl (5 N) and extracted with EtOAc (20 mL×2), and the combined organics are dried (Na2SO4), concentrated and purified on silica gel chromatography column with EtOAc/Hexanes (50/50) to yield the acid as white solid (14 mg). MS (ES): 478.2; the structure is also confirmed by proton NMR.

Workup

  1. extractionextracted with EtOAc (20 mL×2)
  2. dry with materialthe combined organics are dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified on silica gel chromatography column with EtOAc/Hexanes (50/50)

Sources & evidence

ORD record
ord-2b04828a247d4f07964fedd4b8cf9358
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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