Lithium Hydroxide → HCID 21310527, compound

HRID 583411Notes

Reaction equation

HRID 583411 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][CH2:6][CH:7]([N:19]([CH3:36])[C:20](=[O:35])[C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH3:18])[CH:10]=1)C.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:36][N:19]([CH:7]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH3:18])[CH:10]=1)[CH2:6][CH2:5][C:4]([OH:37])=[O:3])[C:20](=[O:35])[C:21]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[C:23]([C:31]([F:32])([F:33])[F:34])[CH:22]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86754325HCID 86754325, compound

Product 1

HCID 21310527HCID 21310527, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 15 g of 4-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5(1-methyl-indol-3-yl)-pentanoic acid ethyl ester and 1.78 g of lithium hydroxide in 102.5 ml of tetrahydrofuran/methanol/water =2/2/1 is stirred at room temperature for 3 hours and then concentrated by evaporation. The residue is dissolved in 150 ml of water, extracted with ether, acidified to pH=2 with 0.1N hydrochloric acid and extracted three times with ether. The combined organic phases originating from the extraction of the acidic aqueous phase are washed with water and saturated NaCl solution, dried (magnesium sulfate) and concentrated by evaporation. In this way the title compound is obtained in the form of a yellow foam. Rf value=0.10 (ethyl acetate/hexane 1:1).

Workup

  1. concentrationconcentrated by evaporation
  2. dissolutionThe residue is dissolved in 150 ml of water
  3. extractionextracted with ether
  4. extractionextracted three times with ether
  5. extractionThe combined organic phases originating from the extraction of the acidic aqueous phase
  6. washare washed with water and saturated NaCl solution
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-af3c973e686543d08b3f2d14dbaeec18
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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