반응 #613091

반응 방정식

(E)-tert-butyl N,N′-diisopropylcarbamimidate

(R)-2,5-dioxotetrahydrofuran-3-yl 2,2,2-trifluoroacetate

(4-methoxyphenyl)methanol

→

(R)-4-tert-butyl 1-(4-methoxybenzyl) 2-hydroxysuccinate

수율 50.2%

용매

Dichloromethane

반응 조건

후처리

1. 1
   추출extracted three times with 10% aqueous solution of NaHCO3
2. 2
   세척The combined aqueous extracts were washed with DCM
3. 3
   추출extracted with DCM
4. 4
   건조The organic layer was dried over sodium sulfate
5. 5
   여과filtered
6. 6
   workup.STIRRINGThe mixture was stirred at rt overnight
7. 7
   기타The precipitate was removed by filtration
8. 8
   기타the filtrate was purified by normal phase automatic silica column chromatography (Combiflash RF)
9. 9
   세척eluting with EA/Hexane (10-80%)

실험 절차

To a solution of (R)-2,5-dioxotetrahydrofuran-3-yl 2,2,2-trifluoroacetate (85 g, 401 mmol) in Dichloromethane (DCM) (600 mL) was added (4-methoxyphenyl)methanol (150 mL, 1202 mmol). The mixture was stirred at rt for 3 h and then extracted three times with 10% aqueous solution of NaHCO3. The combined aqueous extracts were washed with DCM, acidified to pH 2 with 2 N HCl, and then extracted with DCM. The organic layer was dried over sodium sulfate and filtered. To the filtrate was added (E)-tert-butyl N,N′-diisopropylcarbamimidate (161 g, 802 mmol) dropwise over 1 h. The mixture was stirred at rt overnight. The precipitate was removed by filtration and the filtrate was purified by normal phase automatic silica column chromatography (Combiflash RF), eluting with EA/Hexane (10-80%) to afford (R)-4-tert-butyl 1-(4-methoxybenzyl) 2-hydroxysuccinate (62.5 g, 201 mmol, 50.2% yield) as a colorless oil. LCMS: (M+Na)+: 333.1

출처