Lithium Hydroxide → N-(5-hydroxy-2-methoxyphenyl)-N-(2-morpholinoethyl)methanesulfonamide

HRID 1776590Notes

Reaction equation

HRID 1776590 reaction equation
C(=O)([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([N:14]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=1)OCC.[Li+].[OH-]>CO>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([N:14]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86679541ethyl 4-methoxy-3-(N-(2-morpholinoethyl)-methylsulfonamido)-phenyl carbonate

Product 1

HCID 86679542N-(5-hydroxy-2-methoxyphenyl)-N-(2-morpholinoethyl)methanesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-methoxy-3-(N-(2-morpholinoethyl)-methylsulfonamido)-phenyl carbonate (0.250 g, 0.621 mmol) in MeOH (5 ml), LiOH 1M (1.242 ml, 1.242 mmol) was added, and the mixture was stirred at RT for 4 hours. The volatiles were removed under vacuum, and the solid residue was partitioned between EtOAc and a diluted aqueous solution of HCl (pH=5). The organic layer was dried over Na2SO4, the solvent was evaporated and the crude was purified by chromatography on silica gel column (DCM:MeOH=10:0.2) affording N-(5-hydroxy-2-methoxyphenyl)-N-(2-morpholinoethyl)methanesulfonamide (0.180 g, 0.545 mmol, 88% yield, MS/ESI+ 331.0 [MH]+).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe solid residue was partitioned between EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was evaporated
  5. customthe crude was purified by chromatography on silica gel column (DCM:MeOH=10:0.2)

Sources & evidence

ORD record
ord-0221caab13be4adbb1fcf166c3631aa0
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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