Methanol → 5-Acetyl-N-methyl-N-propyl-isophthalamic acid

HRID 1454192Notes

Reaction equation

HRID 1454192 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14](=[O:20])[N:15]([CH3:19])[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:20])[N:15]([CH3:19])[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 57529321HCID 57529321, compound

Product 1

HCID 575292855-Acetyl-N-methyl-N-propyl-isophthalamic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-acetyl-5-(methyl(propyl)carbamoyl)benzoate (107 mg, 0.386 mmol) in a mixture of THF (0.4 mL), MeOH (0.8 mL) and H2O (2.0 mL), was added LiOH (28 mg, 1.159 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 which was ready for next step without further purification: HPLC retention time: 1.412 min (method A). MS (ESI) (M+H)+ 264.18.

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-c95bd4f091954cf8b40e9b806f2b1fd0
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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