반응 #335262

반응 방정식

N-methylmorpholine

(+)-4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid

1,3-dipropyl-5,6-diaminouracil

isobutyl chloroformate

→

title compound

수율 72.5%

(+)-2-[[4-[3-[(6-Amino-1-propyl-1,2,3,4-tetrahydro-3-propyl-2,4-dioxo-5-pyrimidinyl)amino]-2-methyl-3-oxopropyl]phenyl]oxy]-acetic acid, 1,1-dimethylethyl ester

수율 72.5%

용매

chloroform

tetrahydrofuran

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGstir for 6 hours at -20° C
2. 2
   온도Warm to room temperature
3. 3
   세척Wash with saturated sodium hydrogen carbonate (300 mL)
4. 4
   건조Dry (MgSO4)
5. 5
   기타evaporate the solvent in vacuo
6. 6
   기타Purify by flash chromatography (5→10→15→20% isopropanyl/hexane)

실험 절차

Dissolve (+)-4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid (3.02 g, 10.27 mmol) in tetrahydrofuran (100 mL) and treat with N-methylmorpholine (1.2 mL, 10.27 mmol). Cool to -20° C., add isobutyl chloroformate (1.35 mL, 10.27 mmol) and stir for 1 hour. Add a solution of 1,3-dipropyl-5,6-diaminouracil (2.33 g, 10.27 mmol) in dimethylformamide (8 mL) and stir for 6 hours at -20° C. Warm to room temperature and dilute with chloroform (600 mL). Wash with saturated sodium hydrogen carbonate (300 mL), then brine (3×300 mL). Dry (MgSO4) and evaporate the solvent in vacuo. Purify by flash chromatography (5→10→15→20% isopropanyl/hexane) to give the title compound as a foam (3.74 g, 72%); [α]d 20 =+51.4° (C=1.03, CHCl3).

출처