Réaction #86602

Équation de réaction

(S,E)-2-(tert-butoxycarbonylamino)-7-ethoxy-7-oxohept-5-enoic acid

HATU

DIPEA

2-(3-amino-2-oxopyridin-1(2H)-yl)-N-(2-ethyl-butyl)acetamide

2-(3-Amino-2-oxopyridin-1(2H)-yl)-N-(2-ethylbutyl)acetamide

DIPEA

→

(S,E)-Ethyl 6-(tert-butoxycarbonylamino)-7-(1-(2-(2-ethylbutylamino)-2-oxoethyl)-2-oxo-1,2-dihydropyridin-3-ylamino)-7-oxohept-2-enoate

Solvants

DMF

DMF

Conditions de réaction

Traitement

1. 1
   Autreis removed in vacuo
2. 2
   Lavagesubsequently washed each three times with 10% citric acid, saturated NaHCO3 solution and brine
3. 3
   SéchageThe organic phase is dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo in dryness
6. 6
   AutreGel is obtained
7. 7
   Autreit is suitable for further processing without further purification

Mode opératoire

A solution of 101 mg of 2-(3-amino-2-oxopyridin-1(2H)-yl)-N-(2-ethyl-butyl)acetamide (2a, 0.40 mmol) in 2.5 mL of DMF is provided. To this solution, a solution of 121 mg of (S,E)-2-(tert-butoxycarbonylamino)-7-ethoxy-7-oxohept-5-enoic acid (ZED775, 0.40 mmol), 152 mg of HATU (0.40 mmol) and 136 μL of DIPEA (2 eq) in 2.5 mL of DMF is added. By successive addition of DIPEA the pH value is adjusted to ca. 7. The reaction mixture is stirred at 40° C. for 1.5 hours and subsequently at RT overnight, before the solvent is removed in vacuo. The obtained residue is taken up in 75 mL of ethyl acetate and subsequently washed each three times with 10% citric acid, saturated NaHCO3 solution and brine. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo in dryness. Gel is obtained and it is suitable for further processing without further purification.

Source