반응 #69347

반응 방정식

compound 3a

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

EDC

HOBT

Hunig's base

4-chlorobenzylamine

→

4a

수율 79.0%

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

수율 79.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred overnight
2. 2
   기타The dichloromethane was removed in vacuo
3. 3
   기타the reaction mixture quenched with aqueous NH4Cl
4. 4
   세척The solution was washed with water and brine
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated under reduced pressure

실험 절차

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.

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