Reacción #1857555

Ecuación de reacción

(6S,7S,Z)-benzyl 2-((tert-butoxycarbonyl)amino)-7-((S)-1-((4-methoxybenzyl)oxy)ethyl)-10-methyl-6-propoxyundec-2-enoate

→

title compound

Rendimiento 73.0%

(2S,6S,7S)-benzyl 2-((tert-butoxycarbonyl)-amino)-7-((S)-1-((4-methoxybenzyl)oxy)ethyl)-10-methyl-6-propoxyundecanoate

Rendimiento 73.0%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe system was purged with N2 for 5 min
2. 2
   OtroThe system was purged with hydrogen gas (200 psi) 3 times
3. 3
   workup.ADDITIONcharged to 200 psi with hydrogen gas
4. 4
   OtroThe hydrogen was evacuated
5. 5
   Otrothe solution was transferred to a round bottom flask
6. 6
   Lavadorinsing with EtOAc (10 mL)
7. 7
   Otrothe solvent was removed under reduced pressure
8. 8
   workup.DISSOLUTIONThe residue was dissolved in DCM (10 mL)
9. 9
   workup.ADDITIONthe resulting solution was treated with Celite® (3 scoopula tip-fulls)
10. 10
    OtroThe solvent was removed under reduced pressure
11. 11
    Otropurified

Procedimiento

A solution of (6S,7S,Z)-benzyl 2-((tert-butoxycarbonyl)amino)-7-((S)-1-((4-methoxybenzyl)oxy)ethyl)-10-methyl-6-propoxyundec-2-enoate (1.50 g, 2.40 mmol) in MeOH (9.59 mL) was added to a 45 mL pressure reactor. The system was purged with N2 for 5 min and then (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium (I) trifluoromethanesulfonate (0.0170 g, 0.0240 mmol) was added. The system was purged with hydrogen gas (200 psi) 3 times, charged to 200 psi with hydrogen gas, and stirred at room temperature for 24 h. The hydrogen was evacuated and the solution was transferred to a round bottom flask rinsing with EtOAc (10 mL), and the solvent was removed under reduced pressure. The residue was dissolved in DCM (10 mL) and the resulting solution was treated with Celite® (3 scoopula tip-fulls). The solvent was removed under reduced pressure and the resulting adsorbed material was directly loaded onto a column and purified using flash column chromatography (40 g SiO2, 0→40% EtOAc/hexanes) to afford the title compound (1.10 g, 1.752 mmol, 73%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.38-7.27 (m, 5H), 7.29-7.21 (m, 2H), 6.90-6.83 (m, 2H), 5.21-5.09 (m, 2H), 5.04 (d, J=8.4 Hz, 1H), 4.47 (d, J=11.3 Hz, 1H), 4.41-4.27 (m, 2H), 3.78 (s, 3H), 3.63-3.52 (m, 1H), 3.38-3.26 (m, 3H), 1.87-1.74 (m, 1H), 1.70-1.17 (m, 22H), 1.16 (d, J=6.2 Hz, 3H), 0.92-0.83 (m, 9H); 13C NMR (101 MHz, CDCl3) δ 172.75, 158.98, 155.35, 135.47, 131.30, 129.09, 128.57, 128.35, 128.20, 113.70, 79.78, 75.02, 71.89, 69.98, 66.92, 55.24, 53.59, 46.51, 38.66, 32.83, 31.98, 28.69, 28.33, 23.83, 23.54, 22.66, 22.64, 22.22, 17.13, 10.84; ESIMS m/z 650 ([M+Na]+).

Fuente