Hydrochloric Acid → (+/-)-3-{4-[2-Cyclohexyl-1-(4'-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-2-hydroxy-propionic acid

HRID 1669278Notes

Reaction equation

HRID 1669278 reaction equation
C([O:3][C:4](=[O:43])[CH:5](C)[CH2:6][NH:7][C:8](=[O:41])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:11](C)[CH:10]=1)C.[Li+].[OH-:45].Cl>C1COCC1>[CH:18]1([CH2:17][CH:16]([C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:38])([F:37])[F:39])=[CH:32][CH:31]=3)=[CH:28][CH:29]=2)[O:15][C:12]2[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][CH:5]([OH:45])[C:4]([OH:3])=[O:43])=[O:41])=[CH:10][CH:11]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67341724(+/-)-3-{4-[2-Cyclohexyl-1-(4'-trifluoromethyl-biphenyl-4-yl)-ethoxy]-3-methyl-benzoylamino}-2-methyl-propionic acid ethyl ester

Product 1

HCID 59729420(+/-)-3-{4-[2-Cyclohexyl-1-(4'-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-2-hydroxy-propionic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-3-methyl-benzoylamino}-2-methyl-propionic acid ethyl ester (0.0571 g, 0.0978 mmol) in THF (1.0 mL) is added LiOH (1N aqueous, 1.0 mL) and stirred at RT for 4 d. The reaction mixture is acidified with 1N HCl (1.0 mL) and extracted with EtOAc (3×10 mL). Combined organic extracts are dried over Na2SO4, filtered, and conc. to provide (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-2-hydroxy-propionic acid (0.0474 g, 87%) as a white foam. MS (ES): 554.3 [M−H]−.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialCombined organic extracts are dried over Na2SO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-0580b0ed254642c6be48f7cc1f9fedb9
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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