Hydrochloric Acid → 2-Methyl-2-(4-{2-[5-Methyl-2-(3-Naphthalen-1-yl-Phenyl)Oxazol-4-yl]Ethoxy}-Phenoxy)Propionic Acid

HRID 398114Notes

Reaction equation

HRID 398114 reaction equation
C([O:3][C:4](=[O:40])[C:5]([CH3:39])([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH:32]=[CH:31][CH:30]=4)[CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:10][CH:9]=1)[CH3:6])C.[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)C>[CH3:39][C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]4[C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH:32]=[CH:31][CH:30]=4)[CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:12][CH:13]=1)([CH3:6])[C:4]([OH:40])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 698712302-Methyl-2-(4-{2-[5-methyl-2-(3-naphthalen-1-ylphenyl)oxazol-4-yl]ethoxy}phenoxy)propionic acid ethyl ester

Product 1

HCID 129668372-Methyl-2-(4-{2-[5-Methyl-2-(3-Naphthalen-1-yl-Phenyl)Oxazol-4-yl]Ethoxy}-Phenoxy)Propionic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 2-methyl-2-(4-{2-[5-methyl-2-(3-naphthalen-1-ylphenyl)oxazol-4-yl]ethoxy}phenoxy) propionic acid ethyl ester (0.711 mmol) in ethanol (8.9 mL) was treated with NaOH (aq) (0.854 mL of a 5M solution), and heated at reflux for 1 h. The hot solution was acidified to pH 1 with 1M HCl (6 mL). The mixture was cooled to ambient temperature, then further cooled to 0° C. before filtering the product. Following washing with H2O, the product was dried under vacuum at 50° C. to yield a white, crystalline solid: Rf=0.22 in 6:4 ethyl acetate:hexanes; 1H NMR (400 MHz, CDCl3) δ8.08 (s, 1H), 8.03 (d, J=8.8 Hz, 1H), 7.90-7.82 (m, 3H), 7.53-7.39 (m, 6H), 6.86-6.75 (m, 4H), 4.16 (t, J=6.4 Hz, 2H), 2.95 (t, J=6.4 Hz, 2H), 2.35 (s, 3H), 1.47 (s, 6H); MS (EI) 508.1 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. temperaturefurther cooled to 0° C.
  4. filtrationbefore filtering the product
  5. washFollowing washing with H2O
  6. customthe product was dried under vacuum at 50° C.
  7. customto yield a white, crystalline solid

Sources & evidence

ORD record
ord-517265b1bbc240c88f8e6a8387e39db9
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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