Lithium Hydroxide → N-Methyl-5-oxazol-2-yl-N-propyl-isophthalamic acid

HRID 1436636Notes

Reaction equation

HRID 1436636 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:16]=[C:15]([C:17]2[O:18][CH:19]=[CH:20][N:21]=2)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[OH-].[Li+]>C1COCC1>[CH3:13][N:9]([CH2:10][CH2:11][CH3:12])[C:7](=[O:8])[C:6]1[CH:5]=[C:4]([CH:16]=[C:15]([C:17]2[O:18][CH:19]=[CH:20][N:21]=2)[CH:14]=1)[C:3]([OH:22])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68816107N-Methyl-5-oxazol-2-yl-N-propyl-isophthalamic acid methyl ester

Product 1

HCID 21085840N-Methyl-5-oxazol-2-yl-N-propyl-isophthalamic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a solution of N-methyl-5-oxazol-2-yl-N-propyl-isophthalamic acid methyl ester (225 mg, 0.74 mmol) in 1 N lithium hydroxide (3.0 mL, 3.0 mmol) and THF (3.0 mL) at room temperature for 3 h. Add water (40 mL) and extract with ethyl acetate (40 mL). Acidify the aqueous with 5 N HCl, extract with ethyl acetate (2×40 mL), dry (magnesium sulfate) and concentrate to give the title compound (213 mg, 100%).

Workup

  1. extractionAdd water (40 mL) and extract with ethyl acetate (40 mL)
  2. extractionextract with ethyl acetate (2×40 mL)
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-b58734e4b5cb4998a4f9ba6188363c00
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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