Hydrochloric Acid → HCID 58765846, compound

HRID 860669Notes

Reaction equation

HRID 860669 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([C:16]2[O:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)=[N:18][C:17]=2[CH:32]([CH3:34])[CH3:33])[CH3:15])=[CH:8][C:7]=1[CH3:35].[OH-].[Na+].Cl>CO.C1COCC1>[CH:32]([C:17]1[N:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:30])([F:31])[F:29])=[CH:23][CH:22]=2)[O:20][C:16]=1[CH:14]([CH3:15])[CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]([CH3:35])[CH:8]=1)([CH3:33])[CH3:34]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69589307HCID 69589307, compound

Product 1

HCID 58765846HCID 58765846, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-{2-[4-isopropyl-2-(4-trifluoromethoxy-phenyl)-oxazol-5-yl]-propoxy}-2-methyl-phenyl)-propionic acid methyl ester (239 mg, 0.473) 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 12 hours. The mixture is neutralized to pH=4 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 (202 mg, 87%). MS (ES): 492.2; 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-4ab585def0514df49115f460bfc46259
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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