Réaction #1857558

Équation de réaction

(2S,6S,7S)-benzyl 2-((tert-butoxycarbonyl)amino)-7-((S)-1-hydroxyethyl)-10-methyl-6-propoxyundecanoate

→

title compound

Rendement 98.1%

(2S,6S,7S)-2-((tert-butoxycarbonyl)amino)-7-((S)-1-hydroxyethyl)-10-methyl-6-propoxyundecanoic acid

Rendement 98.1%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe hydrogen was removed
2. 2
   Filtrationthe reaction was filtered through a plug of Celite®
3. 3
   LavageThe plug was washed with DCM (2×5 mL)
4. 4
   Concentrationthe combined filtrate and washes were concentrated to dryness under reduced pressure

Mode opératoire

A solution of (2S,6S,7S)-benzyl 2-((tert-butoxycarbonyl)amino)-7-((S)-1-hydroxyethyl)-10-methyl-6-propoxyundecanoate (815 mg, 1.61 mmol) and 10% Pd/C (85 mg, 0.803 mmol) in THF (5.35 mL) was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 4 h. The hydrogen was removed using a stream of N2 and the reaction was filtered through a plug of Celite®. The plug was washed with DCM (2×5 mL) and the combined filtrate and washes were concentrated to dryness under reduced pressure to afford the title compound (660 mg, 1.58 mmol, 98%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 5.14 (d, J=8.2 Hz, 1H), 4.36-4.26 (m, 1H), 3.95-3.83 (m, 1H), 3.63-3.52 (m, 1H), 3.49-3.41 (m, 1H), 3.37-3.27 (m, 1H), 1.93-1.81 (m, 2H), 1.79-0.80 (m, 33H) (carboxylic acid peak is very broad (not listed) and alcohol proton is not visible); 13C NMR (101 MHz, CDCl3) δ 175.98, 155.52, 82.43, 79.93, 71.50, 69.42, 53.26, 45.32, 37.36, 32.61, 28.69, 28.31, 28.26, 25.17, 23.16, 22.66, 22.39, 21.82, 10.63; ESIMS m/z 416 ([M−H]−).

Source