Lithium Hydroxide → 3-(Dipropylcarbamoyl)benzoic acid

HRID 732504Notes

Reaction equation

HRID 732504 reaction equation
CO[C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH2:43]([NH:46][CH2:47][CH2:48][CH3:49])[CH2:44][CH3:45].[OH-].[Li+]>C1COCC1.CN(C=O)C.C(OCC)(=O)C>[CH2:43]([N:46]([CH2:47][CH2:48][CH3:49])[C:3](=[O:13])[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])[CH2:44][CH3:45]

Participants

10

Reactant 6

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 8902DipropylamineHCID 757711-HydroxybenzotriazoleHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 1827693-(Dipropylcarbamoyl)benzoic acid

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve isophthalic acid monomethyl ester (2.25 g, 12.5 mmol), 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride (2.88 g, 15 mmol), 1-hydroxybenzotriazole (2.02 g, 15 mmol) and triethylamine (3.03 g, 30 mmol) in THF (50 mL) and DMF (20 mL). Stir at room temperature 15 min and add dipropylamine (1.52 g, 15 mmol). Stir at room temperature 16 h and dilute with ethyl acetate. Wash with 10% aqueous potassium carbonate, 0.1 N citric acid, 1 N lithium chloride and saturated aqueous sodium chloride and concentrate. Dissolve the residue in THF (60 mL), methanol (18 mL) and water (9 mL). Add lithium hydroxide (2.1 g, 50 mmol), stir at room temperature 16 h and concentrate. Partition the residue between diethyl ether and 1 N HCl. Dry (magnesium sulfate) and concentrate to give the title compound as a solid.

Workup

  1. stirringStir at room temperature 16 h
  2. washWash with 10% aqueous potassium carbonate, 0.1 N citric acid, 1 N lithium chloride and saturated aqueous sodium chloride
  3. concentrationconcentrate
  4. dissolutionDissolve the residue in THF (60 mL)
  5. concentrationconcentrate
  6. customPartition the residue between diethyl ether and 1 N HCl
  7. dry with materialDry (magnesium sulfate)
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-cf20dc0ffccd411ca47e35f8f749836e
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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