Reaktion #69347

Reaktionsgleichung

compound 3a

(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid

EDC

HOBT

Hunig's base

4-chlorobenzylamine

→

4a

Ausbeute 79.0%

(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

Ausbeute 79.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred overnight
2. 2
   SonstigeThe dichloromethane was removed in vacuo
3. 3
   Sonstigethe reaction mixture quenched with aqueous NH4Cl
4. 4
   WaschenThe solution was washed with water and brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

A solution of compound 3a (0.402 g, 1.3 mmol), EDC (0.364 g, 1.9 mmol), HOBT (0.256 g, 1.9 mmol), and Hunig's base (0.662 mL, 3.8 mmol) in dichloromethane (17 mL) was cooled to 0° C. and stirred for half an hour. To this solution 4-chlorobenzylamine (0.174 mL, 1.43 mmol) and a catalytic amount of DMAP were added. The reaction was stirred overnight and the reaction progress was monitored by TLC. The dichloromethane was removed in vacuo and the reaction mixture quenched with aqueous NH4Cl. The solution was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give well formed white crystals of 4a (0.443 g, 79%). 1H NMR (500 MHz, CDCl3): δ ppm 7.31-7.36 (m, 2H) 7.21-7.29 (m, 5H) 7.17-7.21 (m, 2H) 6.09 (t, J=5.6 Hz, 1H) 5.73-5.82 (m, 1H) 5.04-5.10 (m, 2H) 4.65 (ddd, J=13.3, 6.7, 3.4 Hz 1H) 4.41 (dd, J=15.2, 5.9 Hz, 1H) 4.34 (dd, J=14.9, 5.9 Hz, 1H) 4.23-4.30 (m, 1H) 4.23-4.30 (m, 1H) 4.14-4.18 (m, 2H) 3.28 (dd, J=13.7, 2.9 Hz, 1H) 2.66-2.80 (m, 2H) 2.41-2.51 (m, 2H) 2.22-2.29 (m, 1H); 13C NMR (126 MHz, CDCl3): δ 175.1, 171.0, 153.4, 137.1, 135.7, 134.8, 133.4, 129.7, 129.3, 129.1, 129.0, 127.5, 118.1, 66.3, 55.7, 43.1, 40.1, 38.0, 37.8, 36.3. HRMS calcd. for C24H25ClN2O4 (M+H) m/z 441.1581, found 441.1581.

Quelle