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

HRID 1776590ノート

反応式

HRID 1776590 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-0221caab13be4adbb1fcf166c3631aa0
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

読み込み中…