4-Methylmorpholine → {1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	4-Methylmorpholine	HCID 7972	—
Edukt	(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid	HCID 2734668	—
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	{2-[3-(Naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl ester	HCID 67280980	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Lösungsmittel	N-methyl-2-pyrrolidone	HCID 13387	—
Produkt	{1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester	HCID 67282206	109,4%

Reaktionsschritte

A solution of Boc-Tle-OH (176 mg, 0.76 mmol) in NMP (3 mL) was cooled to 0° C. and treated with HATU (318 mg, 0.83 mmol) followed by NMM (0.15 mL). After 10 min, 56 (360 mg, 0.76 mmol) in NMP (2 mL) was added. The reaction mixture was allowed to warm to ambient temperature overnight. The solution was diluted with EtOAc, washed successively with 1M HCl, saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to afford 57 (570 mg) which was used without further purification. Mass spectrum, m/z [686.4] (M+H)+.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08481495B2
Quelldatensatz	uspto-grants-2013_07
ORD ID	ord-db4fd30ef2a846c5999572eecb79810b
Quellennotiz	uspto-grants-2013_07