Reaction #1857555

Reaction equation

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

→

title compound

Yield 73.0%

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

Yield 73.0%

Solvents

MeOH

Conditions

Workup

1. 1
   OtherThe system was purged with N2 for 5 min
2. 2
   OtherThe system was purged with hydrogen gas (200 psi) 3 times
3. 3
   workup.ADDITIONcharged to 200 psi with hydrogen gas
4. 4
   OtherThe hydrogen was evacuated
5. 5
   Otherthe solution was transferred to a round bottom flask
6. 6
   Washrinsing with EtOAc (10 mL)
7. 7
   Otherthe 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
    OtherThe solvent was removed under reduced pressure
11. 11
    Otherpurified

Procedure

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]+).

Source