Hydrochloric Acid → (R,E)-methyl 4-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethylamino)-4-oxobut-2-enoate

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Hydrochloric Acid	HCID 313	—
Edukt	Lipoic acid	HCID 6112	—
Edukt	Diisopropylethylamine	HCID 81531	—
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	(E)-methyl 4-(2-aminoethylamino)-4-oxobut-2-enoate	HCID 86655426	—
Lösungsmittel	Acetonitrile	HCID 6342	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Produkt	(R,E)-methyl 4-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethylamino)-4-oxobut-2-enoate	HCID 87351952	64,6%

Reaktionsschritte

The HCl salt of (E)-methyl 4-(2-aminoethylamino)-4-oxobut-2-enoate (0.515 mmol) was taken up in 10 mL of CH3CN along with R-lipoic acid (TCI, 106 mg, 0.515 mmol), HATU (215 mg, 0.567 mmol) and DIEA (270 μL, 1.55 mmol). The resulting reaction mixture was stirred at room temperature for 18 h and diluted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Purification by silica gel chromatography (95% CH2Cl2, 5% MeOH) afforded 120 mg of (R,E)-methyl 4-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethylamino)-4-oxobut-2-enoate. MS (EI) calcd for C15H24N2O4S: 360.12. found 361 (M+1).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08969354B2
Quelldatensatz	uspto-grants-2015_03
ORD ID	ord-d53a65a2298c46f9be9146130daec9c1
Quellennotiz	uspto-grants-2015_03