Hydrochloric Acid → (S)-Benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-4-phenylbutanamido)-4-methylpentanoate

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Hydrochloric Acid	HCID 313	—
Edukt	p-Toluenesulfonic acid	HCID 6101	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	Benzyl L-leucinate	HCID 6451313	—
Edukt	(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid	HCID 7018726	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Lösungsmittel	Dichloromethane	HCID 6344	—
Produkt	(S)-Benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-4-phenylbutanamido)-4-methylpentanoate	HCID 131735341	100%

Reaktionsschritte

Referring to FIG. 45, DIPEA (2 mL, 12 mmol, 2.7 eq) was added to a mixture of Boc-HoPhe-OH (1.25 g, 4.4 mmol, 1 eq). H-Leu-OBn.TsOH (1.75 g, 4.5 mmol, 1.0 eq) and HATU (2 g, 5 mmol, 1.1 eq) in CH2Cl2 (50 mL) and the mixture was stirred for four hours at RT. The mixture was poured into 0.5N aq. HCl and extracted twice with CH2Cl2. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (SiO2, 0-30% EtOAc in heptanes) and product (2.7 g, 100%) was isolated as a colorless oil.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09315542B2
Quelldatensatz	uspto-grants-2016_04
ORD ID	ord-66bf90c18381461b8ec7fc4f78c1ccf0
Quellennotiz	uspto-grants-2016_04