Methanesulfonyl chloride → Methyl 2-(methyl(4-(methylsulfonamido)benzyl)amino)acetate

HRID 1776504ノート

反応式

HRID 1776504 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]([CH3:13])[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:13][N:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:15][CH:14]=1)[CH2:8][C:9]([O:11][CH3:12])=[O:10]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 18472314HCID 18472314、化合物

生成物 1

HCID 86679452Methyl 2-(methyl(4-(methylsulfonamido)benzyl)amino)acetate収率 80.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of methyl 2-((4-aminobenzyl)(methyl)amino)acetate (0.680 g, 3.27 mmol) in pyridine (15 ml) was cooled to 0° C., and methane sulfonylchloride (0.280 ml, 3.59 mmol) was added. The mixture was warmed to RT and stirred for 1 hour. The solvent was removed, and the crude was portioned between DCM and water. The aqueous phase was basified with solid K2CO3 and extracted with EtOAc. The combined organic layers were dried over Na2SO4, and the solvent was evaporated. The crude was filtered on SCX cartridge (DCM/MeOH 1/1; MeOH/conc.aq.NH4OH 90/10). The basic fraction was evaporated to dryness to give methyl 2-(methyl(4-(methylsulfonamido)-benzyl)amino)acetate (0.750 g, 2.62 mmol, 80% yield, MS/ESI+ 287.2 [MH]+).

後処理

  1. customThe solvent was removed
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvent was evaporated
  5. filtrationThe crude was filtered on SCX cartridge (DCM/MeOH 1/1; MeOH/conc.aq.NH4OH 90/10)
  6. customThe basic fraction was evaporated to dryness

出典と根拠

ORDレコード
ord-6039ba55469b4ad284c14072e76c5ff1
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

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