반응 #50043

반응 방정식

L-Proline

phenyl chloroformate

toluene

→

title product

수율 98.0%

N-Cbz-L-proline

수율 98.0%

용매

NaOH

NaOH

반응 조건

후처리

1. 1
   온도while maintaining the reaction temperature at 0° C.
2. 2
   workup.ADDITIONAfter all reactants were added
3. 3
   추출The solution was then extracted with ether
4. 4
   추출extracted with ethyl acetate
5. 5
   건조The extract was dried over Na2SO4
6. 6
   농축concentrated

실험 절차

L-Proline (10 g, 86.6 mmol) was dissolved in 66 mL of 2N NaOH and cooled to 0° C. To this solution were slowly and simultaneously added 34.35 mL of a solution of phenyl chloroformate in toluene (104.2 mmol) and 33 mL of 4N NaOH, over a period of 1 hr, while maintaining the reaction temperature at 0° C. and the pH above 7. After all reactants were added, the reaction was stirred for 6 hr at room temperature. The solution was then extracted with ether. The remaining aqueous layer was neutralized to pH 6-7 with 1N HCl, then extracted with ethyl acetate. The extract was dried over Na2SO4 and concentrated to afford 21.19 g of the title product (98% yield). 1H NMR (CDCl3) δ 9.55 (d, 1H), 7.3 (s, 5H), 5.25 (d, 2H), 4.35 (t, 1H), 4.20 (t, 1H), 1.8-2.2 (m, 4H).

출처