Reaction #1483037

Reaction equation

nicotinic acid

tert-butyl 2-(2-(2-aminoethyl)disulfanyl)ethylcarbamate

EDCI

→

tert-butyl 2-(2-(2-(nicotinamido)ethyl)disulfanyl)ethylcarbamate

Yield 56.0%

Solvents

CH3CN

EtOAc

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   WashThe organic layer was washed with dilute aqueous NaHCO3, brine
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherPurification by silica gel chromatography (CH2Cl2)

Procedure

Separately, nicotinic acid (246 mg, 2.0 mmol) was taken up in CH3CN (10 mL) along with tert-butyl 2-(2-(2-aminoethyl)disulfanyl)ethylcarbamate (503 mg, 2.0 mmol), EDCI (422 mg, 2.2 mmol). The resulting reaction mixture was stirred at room temperature for 4 h and then diluted with EtOAc. The organic layer was washed with dilute aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (CH2Cl2) afforded tert-butyl 2-(2-(2-(nicotinamido)ethyl)disulfanyl)ethylcarbamate (400 mg, 56%).

Source