반응 #1479290

반응 방정식

(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pent-4-enoic acid

EDAC.HCl

dimethyl aminopyridine

(1S)-N-isobutyl-1-phenylprop-2-en-1-amine

→

title compound

2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-isobutyl-N-[(1S)-1-phenylprop-2-en-1-yl]pent-4-enamide

용매

DCM

DCM

DCM

반응 조건

후처리

1. 1
   기타RT overnight
2. 2
   추출extracted with 0.1 N HCl
3. 3
   추출The aqueous layer was back extracted with DCM (×2)
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타The resulting residue was purified by column chromatography (20% EtAOc/Hexane)

실험 절차

To a solution of (2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pent-4-enoic acid (467 mg), EDAC.HCl (529 mg), and dimethyl aminopyridine (20 mg) in DCM (10 ml) at −20° C. under N2 was added a solution of (1S)-N-isobutyl-1-phenylprop-2-en-1-amine in DCM (6 ml). The mixture was allowed to stir at −20° C. for 1 hr then RT overnight. The next day the reaction was diluted with DCM and extracted with 0.1 N HCl. The aqueous layer was back extracted with DCM (×2). All organics were combined, dried (Na2SO4), filtered and evaporated. The resulting residue was purified by column chromatography (20% EtAOc/Hexane) to afford the title compound as a mixture of diastereomers in the form of a clear oil (628 mg, 82%). 1H NMR (300 MHz, d6-DMSO) δ 0.50-0.732 (m, 7H), 1.24-1.98 (m, 3H), 2.15-2.26 (m, 1H), 2.73-3.3 (m, 4H), 4.74-5.42 (m, 4H), 5.75-6.24 (m, 3H), 6.99-7.38 (m, 5H), 7.79-7.88 (m, 4H). MS APCI, m/z=417 (M+1), LC/MS, 2.93 min.

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