Lithium Hydroxide → 4-[Isobutyl(propyl)amino]-3-[(methylsulfonyl)amino]benzoic acid

HRID 219823Notes

Reaction equation

HRID 219823 reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:13][CH3:14])=[C:7]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:6]=1)C.[OH-].[Li+]>C1COCC1.O>[CH2:15]([N:11]([CH2:12][CH2:13][CH3:14])[C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:24])=[O:3])=[CH:6][C:7]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67542103HCID 67542103, compound

Product 1

HCID 594958284-[Isobutyl(propyl)amino]-3-[(methylsulfonyl)amino]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl-4-[isobutyl(propyl)amino]-3-[(methylsulfonyl)amino]benzoate (7 g, 0.0196 mol) in THF (70 mL) was added lithium hydroxide (4.12 g, 0.098 mol) and water (70 mL). The reaction mixture was heated at 70° C. for 5 h. The reaction mixture was diluted with water (30 mL), washed with diethyl ether (50 mL). The aqueous layer was acidified with 1M HCl until pH=2, extracted with EtOAc (2×75 mL), washed with brine, dried over sodium sulphate and evaporated to afford the title compound as an off white solid (5.6 g, 86%). 1H NMR: (DMSO-d6, 400 MHz), δ 12.78 (s, 1H), 8.39 (s, 1H), 7.87 (s, 1H), 7.65 (m, 1H), 7.28 (m, 1H), 3.09 (s, 3H), 2.97 (m, 2H) 2.84 (m, 2H), 1.67 (m, 1H), 1.41 (m, 2H), 0.84 (m, 9H). LC/MS (Method A): 329.0 (M+H)+. HPLC (Method B) Rt 4.53 min (purity: 99.12%).

Workup

  1. washwashed with diethyl ether (50 mL)
  2. extractionextracted with EtOAc (2×75 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-396ca243906d4850b08bf9a0aca01fee
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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