Hydrochloric Acid → HCID 11512346, compound

HRID 1669276Notes

Reaction equation

HRID 1669276 reaction equation
C([O:5][C:6](=[O:44])[CH2:7][CH2:8][N:9]([C:11](=[O:43])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:14][CH:13]=1)[CH3:10])(C)(C)C.[Li+].[OH-].Cl>C1COCC1.O>[CH:21]1([CH2:20][CH:19]([C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:40])([F:41])[F:42])=[CH:35][CH:34]=3)=[CH:31][CH:32]=2)[O:18][C:15]2[CH:16]=[CH:17][C:12]([C:11]([N:9]([CH3:10])[CH2:8][CH2:7][C:6]([OH:44])=[O:5])=[O:43])=[CH:13][CH:14]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67342524HCID 67342524, compound

Product 1

HCID 11512346HCID 11512346, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of (±)-3-({4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoyl}-methyl-amino)-propionic acid tert-butyl ester (7.4 mg, 0.012 mmol) in THF (0.5 mL) is added LiOH (1 N aqueous, 0.5 mL) and stirred at 70° C. overnight. The reaction mixture is acidified with 1N HCl (1.0 mL), diluted with water, and extracted with EtOAc (3×5 mL). Combined organic extracts are dried over MgSO4, filtered, and conc. to provide (±)-3-({4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoyl}-methyl-amino)-propionic acid (4.6 mg, 68%) as a clear syrup. MS (ES): 554.2 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×5 mL)
  2. dry with materialCombined organic extracts are dried over MgSO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-87c4e078485b4ed2be11d25fcd563b92
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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