반응 #3805

반응 방정식

N,N'-[dithiobis(2,1-phenylene carbonyl)]bis L-serine

NaOH

→

title compound

3-tert-Butoxy-2-{2-[2-(2-tert-butoxy-1-carboxy-ethylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-propionic acid

용매

methanol

반응 조건

후처리

1. 1
   기타The methanol was removed in vacuo
2. 2
   workup.ADDITIONthe residual was diluted with 5 water
3. 3
   추출extracted with ethyl acetate
4. 4
   workup.ADDITIONwas added
5. 5
   온도to maintain a pH=6-7
6. 6
   기타(2-18 hours)
7. 7
   workup.ADDITIONdilute HCL
8. 8
   workup.ADDITIONwas added to a pH=3
9. 9
   여과The product was collected by filtration
10. 10
    세척washed with water
11. 11
    기타dried
12. 12
    기타was recrystallized from ethyl acetate

실험 절차

A solution of N,N'-[dithiobis(2,1-phenylene carbonyl)]bis L-serine bis[O(1,1-dimethylethyl) bis (1,1-dimethylethyl)ester (1.0 g, 1.4 mmol) from Example 39, in 30 mL methanol was treated with 8 mL of 1N NaOH and allowed to stir for 18 hours. The methanol was removed in vacuo and the residual was diluted with 5 water and extracted with ethyl acetate. A slow stream of oxygen was passed thru the aqueous layer while dilute HCl was added to maintain a pH=6-7. After the disulfide formation was complete (2-18 hours), dilute HCL was added to a pH=3. The product was collected by filtration, washed with water, dried and was recrystallized from ethyl acetate to afford 0.4 g of the title compound, mp 206°-207° C.

출처