Hydrochloric Acid → HCID 22261126, compound

HRID 1609978Notes

Reaction equation

HRID 1609978 reaction equation
C([O:3][C:4](=[O:30])[C:5]([CH3:29])([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+].Cl>CCO>[CH3:29][C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:12][CH:13]=1)([CH3:6])[C:4]([OH:30])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69313539HCID 69313539, compound

Product 1

HCID 22261126HCID 22261126, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)ethylsulfanyl]phenoxy}propionic acid ethyl ester (98 mg, 0.23 mmol) was dissolved in EtOH (10 mL) and 5N NaOH (0.5 mL) was added. The reaction was stirred overnight at rt. The reaction was acidified with 5N HCl and the product was extracted into EtOAc, dried (MgSO4) and concentrated to give 96 mg crude product. Purification by reverse phase HPCL gave 47.5 mg (52%) as a light tan solid: mp 104-106° C., 1H NMR (DMSO-d6) δ 1.47 (s, 6H), 2.26 (s, 3H), 2.71 (t, 2H), 3.16 (t, 2H), 6.78 (d, 2H), 7.30 (d, 2H), 7.48 (m, 3H), 7.90 (m, 2H), 13.08 (br s, 1H).

Workup

  1. extractionthe product was extracted into EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-16e81cca698f4f41892e74908f9366a7
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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