Réaction #2446114

Équation de réaction

1,17-diamino-9-azaheptadecane

N,N′-bis(tert-butoxycarbonyl)-S-methylisothiourea

→

12

1-amino-17-[N2,N3-bis(tert-butoxycarbonyl)guanidino]-9-azaheptadecane

Solvants

THF CH3OH

THF

Conditions de réaction

Traitement

1. 1
   Concentrationthe reaction mixture was concentrated under reduced pressure
2. 2
   Autrethe residue was purified by flash chromatography (6% methanol, 4% triethylamine, 90% ethyl acetate)

Mode opératoire

To a stirred solution of 1,17-diamino-9-azaheptadecane 3 (4.9 g, 15.06 mmol) in THF/CH3OH 5/3 (80 mL) at 50° C., a solution of N,N′-bis(tert-butoxycarbonyl)-S-methylisothiourea (1.456 g, 5.02 mmol) in THF (25 mL) was added dropwise over 1 h. After 16 h, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (6% methanol, 4% triethylamine, 90% ethyl acetate), affording 12 as a pale yellow oil, 3.51 g (70%).

Source