Sodium Hydroxide → HCID 22246766, compound

HRID 480316Notes

Reaction equation

HRID 480316 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) δ 7.19-7.32 (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-4202627d98a34e9b9d693cbc6fd5d591
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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