Hydrochloric Acid → HCID 66887430, compound

HRID 253358Notes

Reaction equation

HRID 253358 reaction equation
[CH2:1]([C:3](=[CH:9][CH2:10][O:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([O:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])[CH2:13]1)[C:4]([O:6]CC)=[O:5])[CH3:2].[OH-].[Na+].Cl>CO.C(OCC)(=O)C>[CH2:1]([C:3](=[CH:9][CH2:10][O:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([O:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])[CH2:13]1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66889113HCID 66889113, compound

Product 1

HCID 66887430HCID 66887430, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.5 g of ethyl 2-ethyl-4-{(1R,3S)-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxy}but-2-enoate is dissolved in 5 ml of methanol, and 2.5 ml of a 1N aqueous sodium hydroxide solution are added After 12 h of stirring at room temperature, the mixture is acidified with 3 ml of 1N hydrochloric acid and the resulting precipitate is taken up in ethyl acetate. The solvent is removed under reduced pressure and the residue of the ester hydrolysis, 2-ethyl-4-{(1R,3S)-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxy}but-2-enoic acid, is obtained as 0.45 g of a white solid. C23H28FNO5 (417.48) MS (ESI): 418 (M+H+)

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue of the ester hydrolysis, 2-ethyl-4-{(1R,3S)-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxy}but-2-enoic acid

Sources & evidence

ORD record
ord-640fad2fca284be69662e0c860704edd
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

Loading…