Reaktion #2172053

Reaktionsgleichung

4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonyl chloride

sarcosine t-butyl ester hydrochloride

→

tert-butyl [[(4-{[3-(4-chlorophenyl)-2-propynyl]oxy}phenyl)sulfonyl](methyl)amino]acetate

Ausbeute 53.0%

Lösungsmittel

chloroform

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react overnight at room temperature
2. 2
   EinengenThe reaction was concentrated in vacuo
3. 3
   workup.ADDITIONdiluted with water/ethyl acetate
4. 4
   Extraktionextracted with EtOAc (2×)
5. 5
   WaschenThe combined organics were washed with brine
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto afford a yellow oil which
10. 10
    Sonstigewas purified via flash chormatography

Vorschrift

A solution of 0.57 g (1.67 mmol) of 4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonyl chloride and 0.61 g (3.34 mmol, 2 eq) of sarcosine t-butyl ester hydrochloride in 0.51 mL of pyridine and 15 mL of chloroform was allowed to react overnight at room temperature. The reaction was concentrated in vacuo, diluted with water/ethyl acetate, neutralized with NaHCO3 and extracted with EtOAc (2×). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to afford a yellow oil which was purified via flash chormatography using 6:1 hexane:ethyl acetate to afford 0.396 g (53%) of tert-butyl [[(4-{[3-(4-chlorophenyl)-2-propynyl]oxy}phenyl)sulfonyl](methyl)amino]acetate as a white solid. Electrospray Mass Spec 450.4 (M+H)+.

Quelle