반응 #1458422

반응 방정식

benzyl O-(diphenyloxyphosphoryl)-DL-homoserinate

(R)3-dodecanoyloxytetradecanoic acid

N-methylmorpholin

isobutyl chloroformate

→

Benzyl 2-[(R)-3-DodecanovIoxytetradecanovlamino]-4-(diphenyloxyphosphoryloxy)butanoate

용매

water

tetrahydrofurane

triethylamine

tetrahydrofurane

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring overnight at room temperature
2. 2
   workup.ADDITIONwere added to the residue
3. 3
   추출The mixture was then extracted with ethyl acetate (2×30 ml)
4. 4
   세척washed in succession with water (20 ml) and brine (20 ml)
5. 5
   건조dried over magnesium sulfate
6. 6
   기타The solvent was evaporated
7. 7
   기타the residue was purified by flash chromatography (hexane-ethyl acetate 2:1, Rf=0.29)

실험 절차

4.284 g (10.07 mmol) of (R)3-dodecanoyloxytetradecanoic acid prepared acccording to the method disclosed in Bull. Chem. Soc. Jpn., 60 (1987), 2205–2214, were dissolved in 30 ml of tetrahydrofurane and the solution was cooled down to −15° C. in an ice-cold brine bath. 1,108 ml (10.07 mmol) of N-methylmorpholin and 1.31 ml (10.07 mmol) of isobutyl chloroformate were then added. Stirring was continued for 30 minutes. To the reaction mixture, there was added 5.724 g (10.07 mmol) of benzyl O-(diphenyloxyphosphoryl)-DL-homoserinate in a mixture of 30 ml of tetrahydrofurane and 5 ml of triethylamine. After stirring overnight at room temperature, the solvent was driven away under vacuum and 20 ml of water were added to the residue. The mixture was then extracted with ethyl acetate (2×30 ml). The organic layers were pooled, washed in succession with water (20 ml) and brine (20 ml) and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by flash chromatography (hexane-ethyl acetate 2:1, Rf=0.29); yield 7.455 g i.e 87.1% m.p. 31.0°–32.1° C., 1H-NMR (CDCl3, 250 MHz), δ in ppm: 7.4–7.1 (m, 15H), 6.90 (2d, 1H, 3J=7.6 Hz, NH), 5.3–5.1 (m, 3H), 4.7 (m, 1H), 4.35 (m, 2H), 2.45 (m, 2H), 2.4–2.1 (m, 4H), 1.6 (m, 4H), 1.4–1.1 (m, 34H), 0.9 (t, 6H). 13C-NMR (CDCl3, 63 MHz), δ in ppm: 173.01, 171.08, 169.66, 150.18, (d, 2JP,C=7.1 Hz), 135.01, 129.60, 128.33, 128.14, 127.96, 125.21, 119.80 (d, 3JP,C=5.0 Hz), 70.69, 67.05, 65.19 (d, 2JP,C=5.6 Hz), 49.13, 40.97, 40.77 (2 diast.), 34.20, 33.98, 33.82, 31.70, 29.42, 29.34, 29.14, 28.94, 25.01, 24.47, 13.91.

출처