تفاعل #714215

معادلة التفاعل

triethylamine

NaHCO3

(S)-2-(tert-butoxycarbonyl(methyl)amino)propanoic acid

1-((S)-2-amino-3-methylbutanoyl)-N-ethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HATU

→

tert-butyl (2S)-1-((2S)-1-(2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

المردود 78.5%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted with EtOAc (10 mL)
2. 2
   تركيزThe EtOAc layer was concentrated in vacuo
3. 3
   أخرىthe crude material was purified by flash chromatography (silica gel, 12 g, 0% to 100% EtOAc in hexanes)

الإجراء التجريبي

To a solution of (S)-2-(tert-butoxycarbonyl(methyl)amino)propanoic acid (40.9 mg, 201 μmol, Eq: 1.5) and 1-((S)-2-amino-3-methylbutanoyl)-N-ethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (39 mg, 134 μmol, Eq: 1.00) in DMF (1 mL) was added HATU (76.6 mg, 201 μmol, Eq: 1.5) followed by triethylamine (30 μL, 215 μmol, Eq: 1.6) and the resulting solution was stirred at rt for 2 h. The reaction was poured into saturated aqueous NaHCO3 (10 mL) and the mixture was extracted with EtOAc (10 mL). The EtOAc layer was concentrated in vacuo and the crude material was purified by flash chromatography (silica gel, 12 g, 0% to 100% EtOAc in hexanes) to give tert-butyl (2S)-1-((2S)-1-(2-(ethylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (50 mg), m/z=476 (M+H).

المصدر