Reaktion #87196

Reaktionsgleichung

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate

DIEA

(S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

HATU

→

(S)-methyl 2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(4-methoxyphenyl)propanoate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature for 30 min
3. 3
   Sonstigethen quenched with sodium bicarbonate (sat.)
4. 4
   Extraktionextracted with ethyl acetate (2×)
5. 5
   Trocknendried with sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

To (S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid (1.00 g, 3.39 mmol) in DMF (10 mL) at 0° C. was added HATU (1.42 g, 3.73 mmol). The mixture was stirred for 5 min to dissolve the solids at which time (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate (0.708 g, 3.39 mmol) and DIEA (1.77 mL, 10.2 mmol) was added. The reaction mixture was stirred at ambient temperature for 30 min then quenched with sodium bicarbonate (sat.), extracted with ethyl acetate (2×), dried with sodium sulfate, filtered, and concentrated to provide crude (S)-methyl 2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(4-methoxyphenyl)propanoate as a yellow oil that was carried forward without further purification. MS (EI) for C26H34N2O7, found 387.1 (M-Boc).

Quelle