Sodium Hydroxide → HCID 22246766, compound

HRID 1699041Notes

Reaction equation

HRID 1699041 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([CH2:18][C:19]2[C:28]3[O:27][CH2:26][CH2:25][O:24][C:23]=3[CH:22]=[CH:21][CH:20]=2)[S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=1)C.[OH-].[Na+]>CO.Cl>[O:24]1[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:18][N:13]([CH2:12][C:8]3[CH:7]=[C:6]([CH2:5][C:4]([OH:29])=[O:3])[CH:11]=[CH:10][CH:9]=3)[S:14]([CH3:17])(=[O:15])=[O:16])[C:28]=2[O:27][CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54361462HCID 54361462, compound

Product 1

HCID 22246766HCID 22246766, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of (3-{[(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-methanesulfonyl-amino]-methyl}-phenyl)-acetic acid ethyl ester (210 mg, 0.5 mmol) in MeOH (3 mL) at 0° C. was added aqueous NaOH (2N, 0.5 mL). The reaction was stirred at room temperature for 16 h and was diluted with 1N HCl. The product was extracted into CH2Cl2 and the organic solution was washed with water followed by brine. The organic solution was dried over MgSO4, filtered, and concentrated to provide the title compound (165 mg). 1H NMR (400 MHz, CDCl3) δ7.19-7.32 (m, 4H), 6.73-6.81 (m, 3H), 4.29 (s, 2H), 4.22 (s, 4H), 4.18 (s, 2H), 3.63 (s, 2H), 2.75 (s, 3H).

Workup

  1. extractionThe product was extracted into CH2Cl2
  2. washthe organic solution was washed with water
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-465da96ee0b64c2aba4765304de73931
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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