Lithium Hydroxide → 5-((2-Cyclopentylethyl)carbamoyl)-2-methylbenzoic acid

HRID 2355102Notes

Reaction equation

HRID 2355102 reaction equation
[CH:1]1([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=2)[C:16]([O:18]C)=[O:17])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.O>[CH:1]1([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH3:21])=[C:15]([CH:20]=2)[C:16]([OH:18])=[O:17])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59381881Methyl 5-((2-cyclopentylethyl)carbamoyl)-2-methylbenzoate

Product 1

HCID 593819165-((2-Cyclopentylethyl)carbamoyl)-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 5-((2-cyclopentylethyl)carbamoyl)-2-methylbenzoate (1.2 g, 4.3 mmol) dissolved in THF (15 mL) was added a solution of LiOH, monohydrate (0.27 g, 6.4 mmol) in water (15 mL). The reaction mixture was stirred at RT for 18 h. THF was removed, the residue was extracted with ether (5 mL) and the layers were separated. To the aqueous layer was added 2N HCl until pH 4-5 (a lot of precipitate formed). The solid was collected by filtration, washed with water, dried to give 5-((2-cyclopentylethyl)carbamoyl)-2-methylbenzoic acid as a white solid. MS (ESI, pos. ion) m/z: 276.2 (M+1).

Workup

  1. customTHF was removed
  2. extractionthe residue was extracted with ether (5 mL)
  3. customthe layers were separated
  4. additionTo the aqueous layer was added 2N HCl until pH 4-5 (a lot of precipitate
  5. customformed)
  6. filtrationThe solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d546fa5afd324fa48be6367a1b2b7f82
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Reaction notes

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