Реакция #86602

Уравнение реакции

(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

Растворители

DMF

DMF

Условия реакции

Обработка

1. 1
   Другоеis removed in vacuo
2. 2
   Промывкаsubsequently washed each three times with 10% citric acid, saturated NaHCO3 solution and brine
3. 3
   СушкаThe organic phase is dried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo in dryness
6. 6
   ДругоеGel is obtained
7. 7
   Другоеit is suitable for further processing without further purification

Методика

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.

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