Reacción #3805

Ecuación de reacción

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

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe methanol was removed in vacuo
2. 2
   workup.ADDITIONthe residual was diluted with 5 water
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   workup.ADDITIONwas added
5. 5
   Temperaturato maintain a pH=6-7
6. 6
   Otro(2-18 hours)
7. 7
   workup.ADDITIONdilute HCL
8. 8
   workup.ADDITIONwas added to a pH=3
9. 9
   FiltraciónThe product was collected by filtration
10. 10
    Lavadowashed with water
11. 11
    Otrodried
12. 12
    Otrowas recrystallized from ethyl acetate

Procedimiento

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.

Fuente