تفاعل #614935

معادلة التفاعل

methyl 4-((4-((S)-2-amino-3-((R)-3,3-dimethyl-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,3-azasilolidin-1-yl)-3-oxopropyl)phenyl)ethynyl)benzoate HCl salt

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

EDC

3H-[1,2,3]-triazolo[4,5-b]pyridin-3-ol

DIEA

→

title compound

المردود 86.0%

Methyl 4-((4-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3-((R)-3,3-dimethyl-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,3-azasilolidin-1-yl)-3-oxopropyl)phenyl)ethynyl)benzoate

المردود 86.0%

المذيبات

DMF

DMF

ethyl acetate

brine

ظروف التفاعل

المعالجة

1. 1
   أخرىThe organic layer was separated
2. 2
   غسيلwashed with brine
3. 3
   تجفيفdried over MgSO4
4. 4
   تركيزconcentrated in vacuo

الإجراء التجريبي

To a solution of (S)-2-((tert-butoxycarbonyl)(methyl)amino)propanoic acid (34 mg, 0.17 mmol) in DMF (2 mL) were added EDC (41 mg, 0.22 mmol) and 3H-[1,2,3]-triazolo[4,5-b]pyridin-3-ol (17 mg, 0.13 mmol), followed by a solution of methyl 4-((4-((S)-2-amino-3-((R)-3,3-dimethyl-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,3-azasilolidin-1-yl)-3-oxopropyl)phenyl)ethynyl)benzoate HCl salt (80 mg, 0.13 mmol) in DMF (2 mL) and DIEA (0.07 mL, 0.38 mmol). The reaction mixture was stirred at rt for 1 h and diluted with ethyl acetate and brine. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow solid (85 mg, 86%). 1H NMR (CDCl3) δ 8.10-7.91 (m, 2H), 7.63-7.50 (m, 2H), 7.40 (d, J=8.1 Hz, 2H), 7.24-7.00 (m, 5.5H), 6.56 (d, J=8.6 Hz, 0.5H), 5.26-5.06 (m, 2.5H), 4.11 (q, J=7.0 Hz, 0.5H), 3.92 (s, 3H), 3.21-2.55 (m, 6H), 2.49 (s, 3H), 2.14-1.70 (m, 5H), 1.47 (s, 9H), 1.31-0.90 (m, 5H), 0.52-0.19 (m, 6H); MS(ESI+) m/z 779.6 (M+H)+.

المصدر