تفاعل #714239

معادلة التفاعل

Diisopropylethylamine

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

(S)-ethyl 1-((S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HATU

→

(S)-ethyl 1-((S)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

المردود 86.3%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىto give a light yellow solution
2. 2
   أخرىThe reaction mixture was partitioned between EtOAc and water
3. 3
   غسيلthe separated organic layer was washed with saturated aqueous NaHCO3 and brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe crude material was purified by flash chromatography (silica gel, 12 g, 0% to 40% EtOAc in hexanes)

الإجراء التجريبي

In a 100 mL round-bottomed flask, (S)-2-(tert-butoxycarbonyl(methyl)amino)propanoic acid (128 mg, 630 μmol, Eq: 1.5), (S)-ethyl 1-((S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (140 mg, 420 μmol, Eq: 1.00) and HATU (240 mg, 630 μmol, Eq: 1.5) were combined with DMF (2 mL) to give a light yellow solution. Diisopropylethylamine (110 μL, 630 μmol, Eq: 1.5) was added and the reaction was stirred at rt over the weekend. The reaction mixture was partitioned between EtOAc and water and the separated organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 0% to 40% EtOAc in hexanes) to give (S)-ethyl 1-((S)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (188 mg), m/z=519 (M+H).

المصدر