Reaktion #739005

Reaktionsgleichung

(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide pentafluorophenol salt

benzyl isocyanate

→

(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-(benzyl)carbamoyl-4-methylvalerohydrazide

Lösungsmittel

ethyl acetate

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   Waschenwashed in sequence with 2M aqueous hydrogen chloride, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
4. 4
   TrocknenThe organic layer was dried over anhydrous magnesium sulphate
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto give a yellow oil
7. 7
   Waschenwashed twice with 0.5% aqueous sodium hydroxide
8. 8
   TrocknenThe organic layer was again dried over anhydrous magnesium sulphate
9. 9
   Sonstigeevaporated

Vorschrift

A solution of 1.09 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide pentafluorophenol salt in 5 ml of pyridine was treated with 0.25 ml of benzyl isocyanate under a nitrogen atmosphere. The mixture was stirred for 2 hours at room temperature and then evaporated. The residue was dissolved in ethyl acetate and washed in sequence with 2M aqueous hydrogen chloride, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulphate and evaporated to give a yellow oil. This was dissolved in ethyl acetate and washed twice with 0.5% aqueous sodium hydroxide and then with saturated aqueous sodium chloride. The organic layer was again dried over anhydrous magnesium sulphate and evaporated to give 0.946 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-(benzyl)carbamoyl-4-methylvalerohydrazide in the form of a pale yellow foam.

Quelle