Hydrochloric Acid → 2-Methyl-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3-propyl-phenyl}-2-phenoxy-propionic Acid

HRID 585202Notes

Reaction equation

HRID 585202 reaction equation
C([O:3][C:4](=[O:39])[C:5]([CH3:38])([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[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][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:9]([CH2:28][CH2:29][CH3:30])[CH:8]=1)C.[OH-].[Na+].Cl>CCO>[CH3:38][C:5]([O:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)([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:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[C:9]([CH2:28][CH2:29][CH3:30])[CH:8]=1)[C:4]([OH:39])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20823137HCID 20823137, compound

Product 1

HCID 223400002-Methyl-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3-propyl-phenyl}-2-phenoxy-propionic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3-propyl-phenyl}-2-methyl-2-phenoxy-propionic acid ethyl ester in EtOH (1.5 mL) was treated with 5 N NaOH (140 μL) and then warmed to 65° C. After 18 h, the mixture was acidified to pH=1 with 5 N HCl. The mixture was extracted with EtOAc and then the combined organic phases were dried (MgSO4), filtered and concentrated under reduced pressure to yield the title product. MS (EI) 500.2 (M+H)+; LC RT=3.22 min (>99% pure).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8baa3f43f734449a8668775d991ab0f6
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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