反応 #62894

反応方程式

7-bromo-6-methylthioquinazolin-4(3H)-one formic acid salt

sodium methoxide

allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate

→

title compound

Allyl trans-2-[3-(7-Bromo-6-methylthioquinazolin-4(3H)-on-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate

溶媒

methanol

methanol

反応条件

後処理

1. 1
   その他Under a nitrogen atmosphere in a flame dried flask at room temperature
2. 2
   その他the reaction mixture was evaporated under reduced pressure
3. 3
   抽出The aqueous solution was extracted three times with 15 ml portions of dichloromethane
4. 4
   乾燥The combined extracts were dried over anhydrous sodium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated

実験手順

Under a nitrogen atmosphere in a flame dried flask at room temperature and with magnetic stirring, a suspension of 0.43 g (0.00136 mol) of 7-bromo-6-methylthioquinazolin-4(3H)-one formic acid salt in 5 ml of methanol was treated with two equivalents of sodium methoxide in methanol (approximately 1N). After 15 minutes 0.53 g (0.0016 mol) of allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate was added in one portion. After being stirred for an hour, the reaction mixture was evaporated under reduced pressure, and the residue was taken up in about 15 ml of water. The aqueous solution was extracted three times with 15 ml portions of dichloromethane. The combined extracts were dried over anhydrous sodium sulfate, filtered, and evaporated to afford the title compound: yield 0.61 g (86%). 1H-NMR(CDCl3): 1.3-2.0 ppm (multiplet, 4H, CH3OCHCH2CH2CH2N), 2.6 (singlet, 3H, CH3S), 2.8-3.0 (multiplet, 4H, COCH2CH and NCH2), 3.3 (broad singlet, 1H, CH2CHNCO), 3.4 (singlet, 3H CH3O), 4.0 (broad doublet, 1H, CHOCH3), 4.6 (broad doublet 2H, CH2CH=CH2), 4.8-5.1 (multiple peaks, 2H, NCH2CO), 5.2-5.4 (multiplet, 2H, CH2 =CH), 5.9 (octet, 1H, CH=CH2), 7.3 (singlet, 1H, aromatic H), 7.9 (singlet, 1H, aromatic H), 7.95 (singlet, 1H, N=CH--N).

出典