Reacción #57464

Ecuación de reacción

tert-butyl N-[(1S,2R)-1-benzyl-4-(cyclopentyloxy)-2-hydroxy-4-(6-quinoxalinylsulfonyl)butyl]carbamate

trifluoroacetic acid

→

(3R,4S)-4-amino-1-(cyclopentyloxy)-5-phenyl-1-(6-quinoxalinylsulfonyl)-3-pentanol

Rendimiento 82.4%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe acid was removed in vacuo
2. 2
   Otrothe residue was partitioned between dichloromethane and 1N sodium hydroxide
3. 3
   OtroThe organic layer was separated
4. 4
   Extracciónthe aqueous layer was extracted again with dichloromethane
5. 5
   SecadoThe combined organic layers were dried over anhydrous sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated in vacuo
8. 8
   OtroThe crude product was purified on flash grade silica gel eluting with dichloromethane:methanol (98:2)
9. 9
   workup.ADDITIONFractions containing the product
10. 10
    Otroevaporated in vacuo
11. 11
    Otrodried under high vacuum

Procedimiento

A mixture of tert-butyl N-[(1S,2R)-1-benzyl-4-(cyclopentyloxy)-2-hydroxy-4-(6-quinoxalinylsulfonyl)butyl]carbamate (563 mg, 1.01 mmol) and trifluoroacetic acid (5 mL) was stirred under an Argon atmosphere for 0.5 hrs. The acid was removed in vacuo and the residue was partitioned between dichloromethane and 1N sodium hydroxide. The organic layer was separated and the aqueous layer was extracted again with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The crude product was purified on flash grade silica gel eluting with dichloromethane:methanol (98:2). Fractions containing the product were combined and evaporated in vacuo and dried under high vacuum to provide (3R,4S)-4-amino-1-(cyclopentyloxy)-5-phenyl-1-(6-quinoxalinylsulfonyl)-3-pentanol as a foam (379 mg, 82%). H1-NMR (chloroform-D3): 1.66 (m, 11H), 2.51 (m, 1H), 2.86 (m, 1H), 3.07 (m, 1H), 3.23 (m, 1H), 3.32 (m, 1H), 3.84 (m, 1H), 4.90 (m, 1H), 7.20 (m, 5H), 8.16 (m, 1H), 8.28 (d, 1H), 8.70 (m, 1H), 8.99 (m, 2H). MS (ESI): 457 (M+H).

Fuente