반응 #335265

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 66.0%

(-)-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 66.0%

용매

chloroform

tetrahydrofuran

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGStir at -20° C. for 3 hours
2. 2
   온도warm to room temperature
3. 3
   workup.STIRRINGStir for 2 hours
4. 4
   기타Separate the organic phase
5. 5
   세척wash with saturated sodium hydrogen carbonate (300 mL)
6. 6
   건조Dry (Na2SO4)
7. 7
   기타evaporate the solvent in vacuo
8. 8
   기타to give 4.31 g crude product
9. 9
   기타Purify by flash chromatography (10→15→20% isopropanol/hexane)

실험 절차

Dissolve (-)-4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid (1.92 g, 6.52 mmol) in tetrahydrofuran (50 mL) and treat with N-methylmorpholine (0.77 mL, 6.52 mmol). Cool to -20° C. and treat with isobutyl chloroformate (0.86 mL, 6.52 mmol). Stir for 1 hour and add a solution of 1,3-dipropyl-5,6-diaminouracil (1.48 g, 6.52 mmol) in dimethylformamide (4 mL). Stir at -20° C. for 3 hours and warm to room temperature. Stir for 2 hours and dilute with chloroform (400 mL). Separate the organic phase and wash with saturated sodium hydrogen carbonate (300 mL), then brine (2×400 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give 4.31 g crude product. Purify by flash chromatography (10→15→20% isopropanol/hexane) to give the title compound (2.16 g, 66%); [α]d 20 =-45.8 ° (C=1.00, CHCl3).

출처