Lithium hydroxide, monohydrate → 3-[(Dipropylamino)carbonyl]-5-Ethylbenzoic Acid

HRID 14003

Reaction equation

HRID 14003 reaction equation
O.[OH-].[Li+].[CH2:4]([N:7]([CH2:22][CH2:23][CH3:24])[C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH2:20][CH3:21])[CH:19]=1)[C:13]([O:15]C)=[O:14])=[O:9])[CH2:5][CH3:6]>C1COCC1.CO.O.O.Cl>[CH2:22]([N:7]([CH2:4][CH2:5][CH3:6])[C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH2:20][CH3:21])[CH:19]=1)[C:13]([OH:15])=[O:14])=[O:9])[CH2:23][CH3:24]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22593628Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

Product 1

HCID 225936423-[(Dipropylamino)carbonyl]-5-Ethylbenzoic Acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
22.5 °C

Procedure

Lithium hydroxide monohydrate (0.0680 g, 1.6 mmol) is added to a mixture of methyl 3-[(dipropylamino)carbonyl]-5-ethylbenzoate (PREPARATION 20, 0.450 g, 1.6 mmol) in a mixture of THF/methanol/water (2/1/1, 8 mL). The mixture is stirred at 20-25 degrees C. for 3 hours. The mixture is then diluted with water (20 mL) and hydrochloric acid (1 N) is added to bring the pH to less than 3. The aqueous mixture is extracted with ethyl acetate. The organic phase is separated and washed with saline, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title compound, MS (ESI+) for C16H23NO3 m/z (M+H)+=278.2.

Workup

  1. additionis added
  2. extractionThe aqueous mixture is extracted with ethyl acetate
  3. customThe organic phase is separated
  4. washwashed with saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a595837486be4e039d4224f92ba8f393
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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