Sodium Hydroxide → (3-{[Methanesulfonyl-(4-methyl-benzyl)-amino]-methyl}-phenyl)-acetic Acid

HRID 2298181Notes

Reaction equation

HRID 2298181 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:7]=1)C.[OH-].[Na+]>CO.Cl.O>[CH3:25][S:22]([N:13]([CH2:12][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([OH:26])=[O:3])[CH:11]=[CH:10][CH:9]=1)[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:24])=[O:23]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53833369(3-{[Methanesulfonyl-(4-methyl-benzyl)amino]-methyl}-phenyl)-acetic acid ethyl ester

Product 1

HCID 22246862(3-{[Methanesulfonyl-(4-methyl-benzyl)-amino]-methyl}-phenyl)-acetic AcidYield 92.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (3-{[methanesulfonyl-(4-methyl-benzyl)-amino)-methyl}-phenyl)-acetic Acid ethyl ester (101.4 mg, 0.27 mmol) in MeOH (3 mL) was added aqueous NaOH (2N, 0.4 mL). The reaction was stirred at room temperature for 1 h and was diluted with a 1:1 mixture of 1N HCl and water. The product was extracted into CH2Cl2 (3×) and the organic solution was dried over MgSO4, filtered, and concentrated to provide the title compound (87 mg). 1H NMR (400 MHz, CDCl3) 6 7.13-7.34 (m, 8H), 4.28 (d, 4H), 3.65 (s, 2H), 2.75 (s, 3H), 2.33 (s, 2H); MS 346 (M−1).

Workup

  1. extractionThe product was extracted into CH2Cl2 (3×)
  2. dry with materialthe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa098834ecdd4e2b9fb689751ecd6325
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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