Reacción #52008

Ecuación de reacción

Intermediate ( 4 )

N-benzyl-N′-[3,5-bis(trifluoromethyl)benzoyl]-N-{[4-(hydroxymethyl)cyclohexyl]methyl}sulfamide

phenyl isocyanate

→

title compound

(4-{[benzyl({[3,5-bis(trifluoromethyl)benzoyl]amino}sulfonyl)amino]methyl}cyclohexyl)methyl phenylcarbamate

Disolventes

water

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed for 24 hours
2. 2
   Extracciónextracted repeatedly with dichloromethane
3. 3
   FiltraciónReconstituted in dichloromethane, filtered off precipitate
4. 4
   Otropurified material
5. 5
   Otroisolated from filtrate by RP-HPLC

Procedimiento

Intermediate (4) (80 mg, 140 μmole, 1.0 eq) was dissolved in acetonitrile (10 mL) and phenyl isocyanate (18 μL, 168 μmole, 1.2 eq) was added. The mixture was refluxed for 24 hours, then diluted with water and extracted repeatedly with dichloromethane. Reconstituted in dichloromethane, filtered off precipitate and purified material isolated from filtrate by RP-HPLC to give title compound. 1H NMR (400 MHz, MeOH-d4): δ 0-75-9.0 (m, 4H), 1.38-1.60 (m, 2H), 1.68-1.84 (m, 4H), 3.21 (d, 2H, J=8 Hz), 3.86 (d, 2H, J=8 Hz), 4.51 (s, 2H), 7.0 (t, 1H, J=8 Hz) 7.17-7.30 (mult, 5H), 7.33-7.7.45 (mult, 4H), 8.11 (s, 1H), 8.42 (s, 2H).

Fuente