Lithium Hydroxide → 4-[N-Methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pentanoic acid

HRID 583414Notes

Reaction equation

HRID 583414 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[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)C.[OH-].[Li+]>CO.O1CCCC1.O>[CH3:36][N:19]([CH:7]([CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[CH2:6][CH2:5][C:4]([OH:37])=[O:3])[C:20](=[O:35])[C:21]1[CH:22]=[C:23]([C:31]([F:33])([F:34])[F:32])[CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 542164914-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pentanoic acid ethyl ester

Product 1

HCID 213105294-[N-Methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pentanoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 19.5 g of 4-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pentanoic acid ethyl ester and 7.8 g of lithium hydroxide (monohydrate) in 212 ml of methanol, 148 ml of tetrahydrofuran and 60 ml of water is stirred at room temperature for 75 minutes and then concentrated by evaporation. The residue is dissolved in 150 ml of water, acidified to pH=2 with 0.1N hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases 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=0.50 (hexane/ethyl acetate 1:4). IR (CH2Cl2): 3053, 1712, 1639, 1406, 1341, 1278, 1183, 1141, 1108, 904, 849, 821 cm-1.

Workup

  1. concentrationconcentrated by evaporation
  2. dissolutionThe residue is dissolved in 150 ml of water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases are washed with water and saturated NaCl solution
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c4669832cb9044dcb43e90b3d795ce41
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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