Hydrochloric Acid → 2-[5-(2,3-Dihydro-indol-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid

HRID 888653Notes

Reaction equation

HRID 888653 reaction equation
C[O:2][C:3](=[O:34])[CH:4]([C:9]1[CH:10]=[C:11]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:12]=[C:13]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16]2)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].CO.[Li+].[OH-].Cl>C1COCC1>[N:15]1([C:13]2[CH:14]=[C:9]([CH:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:34])=[O:2])[CH:10]=[C:11]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][CH:25]=3)[CH:12]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 576666612-[5-(2,3-Dihydro-indol-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester

Product 1

HCID 252697802-[5-(2,3-Dihydro-indol-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acidYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[5-(2,3-dihydro-indol-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester, MeOH (1 mL), THF (1 mL) and 10% aq. LiOH solution (0.5 mL) was stirred at 40° C. overnight. The solution was then acidified with aq. 2M HCl and extracted with DCM (3×1 mL). The organic layers were filtered through PTFE filter and concentrated to yield an oil. The residue was purified using reverse phase preparative HPLC (H2O: MeCN) to give the title product in 8% yield as a yellow oil.

Workup

  1. extractionextracted with DCM (3×1 mL)
  2. filtrationThe organic layers were filtered through PTFE
  3. filtrationfilter
  4. concentrationconcentrated
  5. customto yield an oil
  6. customThe residue was purified

Sources & evidence

ORD record
ord-767329f8312c434eaa8c3fc418f19cb4
Source dataset
uspto-grants-2012_08
Patent number
US08247610B2

Reaction notes

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