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

HRID 1776504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776504
[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]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 18472314HCID 18472314, Verbindung

Produkt 1

HCID 86679452Methyl 2-(methyl(4-(methylsulfonamido)benzyl)amino)acetateAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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]+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6039ba55469b4ad284c14072e76c5ff1
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265768B2

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