반응 #797059

반응 방정식

magnesium monoxide

(S)-2-(6-Heptyloxyquinazolin-2-yl)propyl carbamate

toluene

iodobenzene diacetate

→

desired product

수율 15.0%

(R)-4-(6-Heptyloxyquinazolin-2-yl)-4-methyloxazolidin-2-one

수율 15.0%

14

(S)-2-(6-Heptyloxyquinazolin-2-yl)propyl carbamate

용매

DCM

반응 조건

후처리

1. 1
   여과the reaction mixture was filtered
2. 2
   기타The crude mixture was then purified via chromatography (SiO2, 12 g, 0-80% ethyl acetate/hexanes)

실험 절차

(S)-2-(6-Heptyloxyquinazolin-2-yl)propyl carbamate (14, 350 mg, 0.0010 mol) was dissolved in toluene (20 mL, 0.2 mol), followed by magnesium monoxide (93.9 mg, 0.00233 mol), iodobenzene diacetate (359 mg, 0.00111 mol) and finally Rh2(esp)2 (35 mg, 0.000046 mol). The reaction mixture was then heated at 40° C. for 3 days. DCM was added to the reaction mixture, and the reaction mixture was filtered. The crude mixture was then purified via chromatography (SiO2, 12 g, 0-80% ethyl acetate/hexanes) to give 53 mg of the desired product (15%) and 215.0 mg of 14. 1H NMR (CHLOROFORM-d) δ: 9.27 (s, 1H), 7.90 (d, J=9.3 Hz, 1H), 7.58 (dd, J=9.2, 2.6 Hz, 1H), 7.15 (d, J=2.5 Hz, 1H), 6.19 (br. s., 1H), 5.18 (d, J=8.5 Hz, 1H), 4.49 (d, J=8.8 Hz, 1H), 4.11 (t, J=6.5 Hz, 2H), 1.80-1.97 (m, 2H), 1.76 (s, 3H), 1.21-1.60 (m, 8H), 0.91 (t, J=6.7 Hz, 3H). MS (M+1): 344.30.

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