Lithium Hydroxide → HCID 86616205, compound

HRID 426342Notes

Reaction equation

HRID 426342 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([C:10]1[CH:11]=[C:12]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[C:18]([F:27])[CH:17]=2)[CH:15]=1)[CH2:5][CH:6]([CH2:8][CH3:9])[CH3:7].[Li+].[OH-]>CO.O>[F:27][C:18]1[CH:17]=[C:16]([C:14]2[CH:15]=[C:10]([CH:4]([CH2:5][CH:6]([CH2:8][CH3:9])[CH3:7])[C:3]([OH:38])=[O:2])[CH:11]=[C:12]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:32][CH:33]=3)[CH:13]=2)[CH:21]=[CH:20][C:19]=1[O:22][C:23]([F:25])([F:24])[F:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86616206HCID 86616206, compound

Product 1

HCID 86616205HCID 86616205, compoundYield 564.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 2-(3-fluoro-4-trifluoromethoxy-4″-trifluoromethyl-[1,1′;3′,1″]terphenyl-5′-yl)-4-ethyl-pentanoic acid methyl ester (2 mg) THF (1 mL), 10% LiOH in MeOH (0.3 mL) and H2O (0.3 mL) was stirred at 30° C. for 3 h. The solution was concentrated in vacuo and the residue was diluted with H2O and then acidified with concentrated HCl. The aqueous solution was extracted with DCM and filtered through polytetrafluoroethylene filter. The solution was concentrated in vacuo to give a solid residue. The solid was purified using reverse phase preparative HPLC (MeCN, H2O) to give the title product (11 mg, 44%).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionthe residue was diluted with H2O
  3. extractionThe aqueous solution was extracted with DCM
  4. filtrationfiltered through polytetrafluoroethylene
  5. filtrationfilter
  6. concentrationThe solution was concentrated in vacuo
  7. customto give a solid residue
  8. customThe solid was purified

Sources & evidence

ORD record
ord-3e051cade5c64dad97a71ca1a0f07d79
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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