Hydrochloric Acid → 2-(4-{2-[2-(4'-Formylbiphenyl-3-yl)-5-Methyloxazol-4-yl]Ethoxy}Phenoxy)-2-Methylpropionic Acid

HRID 398116Notes

Reaction equation

HRID 398116 reaction equation
C([O:3][C:4](=[O:38])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[C:26]([C:30]4[CH:35]=[CH:34][C:33]([CH:36]=[O:37])=[CH:32][CH:31]=4)[CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)C>[CH:36]([C:33]1[CH:32]=[CH:31][C:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:20]3[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]4[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:38])=[O:3])=[CH:14][CH:13]=4)[N:19]=3)[CH:25]=2)=[CH:35][CH:34]=1)=[O:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 865874062-(4-{2-[2-(4'-Formylbiphenyl-3-yl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methyl propionic acid ethyl ester

Product 1

HCID 226334302-(4-{2-[2-(4'-Formylbiphenyl-3-yl)-5-Methyloxazol-4-yl]Ethoxy}Phenoxy)-2-Methylpropionic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 2-(4-{2-[2-(4′-formylbiphenyl-3-yl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methyl 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=0.14 in 6:4 ethyl acetate:hexanes; MS (EI) 486.1 (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-2a47cb307fd54d9eb08a78c113342bab
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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