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

https://huagongshe.com/de/reaction/58918

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-	HCID 90234	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	(S)-2-Tert-butoxycarbonylamino-3-(4-methoxy-phenyl)-propionic acid methyl ester	HCID 11220582	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	(S)-methyl 2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(4-methoxyphenyl)propanoate	HCID 117690792	—

Reaktionsschritte

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).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09434761B2
Quelldatensatz	uspto-grants-2016_09
ORD ID	ord-fc9688e0467741d18efa5c72106a65cf
Quellennotiz	uspto-grants-2016_09