Hydrochloric Acid → HCID 11613554, compound

HRID 1669271Notes

Reaction equation

HRID 1669271 reaction equation
C([O:5][C:6](=[O:43])[CH2:7][CH2:8][NH:9][C:10](=[O:42])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=3)=[CH:28][CH:27]=2)[CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:13][CH:12]=1)(C)(C)C.[Li+].[OH-].Cl>C1COCC1>[CH:20]1([CH2:19][CH:18]([C:26]2[CH:27]=[CH:28][C:29]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:34][CH:33]=3)=[CH:30][CH:31]=2)[O:17][C:14]2[CH:15]=[CH:16][C:11]([C:10]([NH:9][CH2:8][CH2:7][C:6]([OH:43])=[O:5])=[O:42])=[CH:12][CH:13]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59729396HCID 59729396, compound

Product 1

HCID 11613554HCID 11613554, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-propionic acid tert-butyl ester (Isomer 1) (0.0999, 0.168 mmol) in THF (1.7 mL) is added LiOH (1 N aqueous, 1.7 mL) and stirred at 70° C. overnight. The reaction mixture is acidified with 1N HCl (2.0 mL) and extracted with EtOAc (3×10 mL). Combined organic extracts are dried over MgSO4, filtered, and conc. to provide 3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-propionic acid (Isomer 1) (0.0801 g, 88%) as a white solid. MS (ES): 540.0 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialCombined organic extracts are dried over MgSO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ee29c76555bc4f0a9966b341a5ec0541
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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