Lithium Hydroxide → HCID 54390861, compound

HRID 583413Notes

Reaction equation

HRID 583413 reaction equation
C([O:3][C:4](=[O:37])[CH:5]=[CH: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)[CH:6]=[CH: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 54257149HCID 54257149, compound

Product 1

HCID 54390861HCID 54390861, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 9.51 g of 4-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(1-methyl-indol-3-yl)-pent-2-enoic acid ethyl ester and 1.14 g of lithium hydroxide in 65 ml of tetrahydrofuran/methanol/water =2/2/1 is stirred at room temperature for 15 hours and then concentrated by evaporation. The residue is dissolved in 150 ml of water with heating to 55°, extracted with ether at 20°, 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=0.13 (ethyl acetate).

Workup

  1. concentrationconcentrated by evaporation
  2. dissolutionThe residue is dissolved in 150 ml of water
  3. temperaturewith heating to 55°
  4. extractionextracted with ether at 20°
  5. extractionextracted three times with ether
  6. extractionThe combined organic phases originating from the extraction of the acidic aqueous phase
  7. washare washed with water and saturated NaCl solution
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e132def9f07c47e5b52e28428be73226
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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