Methanol → 3-Acetyl-5-(dipropylcarbamoyl)benzoic acid

HRID 1454186Notes

Reaction equation

HRID 1454186 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14](=[O:22])[N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH:13]=1)[C:7]([O:9]C)=[O:8])(=[O:3])[CH3:2].CO.O.[Li+].[OH-]>C1COCC1>[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14](=[O:22])[N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH:13]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 57529297Methyl 3-acetyl-5-(dipropylcarbamoyl)benzoate

Product 1

HCID 575292993-Acetyl-5-(dipropylcarbamoyl)benzoic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-acetyl-5-(dipropylcarbamoyl)benzoate (38 mg, 0.125 mmol) in a mixture of THF (0.1 mL), MeOH (0.2 mL) and H2O (0.5 mL), was added LiOH (8.9 mg, 0.374 mmol) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated and partitioned between ethyl acetate and H2O. The aqueous layer was washed with ethyl acetate twice and acidified with 1N HCl solution to pH around 2˜3. The aqueous layer was extracted with ethyl acetate 3 times and the combined organic layers were dried over sodium sulfate and concentrated under vacuum to give the title compound (35 mg, 97.2% yield): 1H NMR (CD3OD, 500 MHz) δ ppm 0.78 (3H, m), 1.03 (3H, t, J=5 Hz), 1.62 (2H, m), 1.77 (2H, m), 2.69 (3H, s), 3.23 (2H, m), 3.52 (2H, m), 8.17 (1H, m), 8.21 (1H, m), 8.68 (1H, m). HPLC retention time: 1.687 min (method A). MS (ESI) (M+H)+ 292.23.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and H2O
  3. washThe aqueous layer was washed with ethyl acetate twice
  4. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-579d42efcf394e1eb7971b956bb2590b
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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