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

HRID 1776504노트

반응식

HRID 1776504 반응식
[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]

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 18472314HCID 18472314, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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]+).

후처리

  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

출처 및 근거

ORD 기록
ord-6039ba55469b4ad284c14072e76c5ff1
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265768B2

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