반응 #1857557

반응 방정식

(2S,6S,7S)-methyl 6-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-7-((S)-1-hydroxyethyl)-10-methylundecanoate

LiOH.H2O

→

title compound

수율 88.3%

(2S,6S,7S)-6-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-7-((S)-1-hydroxyethyl)-10-methylundecanoic acid

수율 88.3%

용매

THF

H2O

EtOAc

HCl

반응 조건

후처리

1. 1
   기타the phases were separated
2. 2
   추출the aq. phase was further extracted with EtOAc (3×15 mL)
3. 3
   세척The combined organic extracts were washed with brine (8 mL)
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated to dryness

실험 절차

To a solution of (2S,6S,7S)-methyl 6-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-7-((S)-1-hydroxyethyl)-10-methylundecanoate (700 mg, 1.46 mmol) in THF (9.73 mL) and H2O (4.87 mL) was added LiOH.H2O (184 mg, 4.38 mmol), and the reaction was stirred at room temperature for 4 h. The reaction was diluted with EtOAc (15 mL) and 0.2 M HCl (15 mL), the phases were separated, and the aq. phase was further extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine (8 mL), dried over Na2SO4, filtered, and concentrated to dryness to afford the title compound (600 mg, 1.289 mmol, 88%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.31-7.21 (m, 5H), 5.63 (s, 1H), 4.57-4.45 (m, 2H), 3.89-3.74 (m, 2H), 3.59-3.52 (m, 1H), 1.92-1.63 (m, 2H), 1.63-0.94 (m, 22H), 0.83 (app dd, J=6.6, 2.1 Hz, 6H) (carboxylic acid and alcohol peaks are very broad (not listed)); 13C NMR (101 MHz, CDCl3) δ 179.67, 156.76, 138.11, 128.33, 128.05, 127.64, 80.99, 79.27, 71.52, 68.79, 56.30, 46.67, 37.81, 32.72, 29.56, 28.48, 28.27, 25.15, 23.19, 22.63, 22.50, 22.21; ESIMS m/z 464 ([M−H]−).

출처