Hydrochloric Acid → HCID 11613554, compound

HRID 1669274Notes

Reaction equation

HRID 1669274 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:10][CH:9]=1.[Li+].[OH-].Cl>C1COCC1>[CH:17]1([CH2:16][CH:15]([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)[O:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:40])=[O:2])=[O:39])=[CH:9][CH:10]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67341070HCID 67341070, compound

Product 1

HCID 11613554HCID 11613554, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-propionic acid methyl ester (0.0834, 0.151 mmol) in THF (1.0 mL) is added LiOH (1 N aqueous, 0.4 mL) and stirred at RT for 1 h. The reaction mixture is acidified with 1N HCl (0.5 mL) 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]-benzoylamino}-propionic acid (0.0814 g, 71%) as a white solid. MS (ES): 540.3 [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-823c9a9ae0404e1c85fe783ddd991d5f
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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