Hydrochloric Acid → HCID 22633469, compound

HRID 398117Notes

Reaction equation

HRID 398117 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[O:19][C:20]([CH3:41])=[C:21]([CH2:23][CH2:24][O:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([C:36]([O:38]CC)=[O:37])([CH3:35])[CH3:34])[CH:27]=4)[N:22]=3)[CH:13]=2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[C:36]([C:33]([CH3:35])([O:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[O:25][CH2:24][CH2:23][C:21]1[N:22]=[C:18]([C:14]2[CH:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:11][CH:10]=3)[CH:17]=[CH:16][CH:15]=2)[O:19][C:20]=1[CH3:41])[CH3:34])([OH:38])=[O:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69871379HCID 69871379, compound

Product 1

HCID 22633469HCID 22633469, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 3′-(4-{2-[3-(1-ethoxycarbonyl-1-methylethoxy)phenoxy]ethyl}-5-methyloxazol-2-yl)-biphenyl-4-carboxylic 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 with1M 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 a white, crystalline solid: mp 184° C.; MS (EI) 525.2 (M+Na)+, 502.2 (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. to a white, crystalline solid

Sources & evidence

ORD record
ord-462964914d1743149edbf895f847d644
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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