4-Methylmorpholine → 2,5,6,10,13-Pentaazatetradecanedioic acid, 12-(1,1-dimethylethyl)-8-hydroxy-3-(1-methylpropyl)-4,11-dioxo-9-(phenylmethyl)-6-((4-(5-thiazolyl)phenyl)methyl)-, dimethyl ester, (3S-(3R(R),8R,9R,12R*))-

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	4-Methylmorpholine	HCID 7972	—
Edukt	O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate	HCID 2733204	—
Edukt	1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane	HCID 10792527	—
Edukt	L-Isoleucine, N-(methoxycarbonyl)-	HCID 28378062	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	2,5,6,10,13-Pentaazatetradecanedioic acid, 12-(1,1-dimethylethyl)-8-hydroxy-3-(1-methylpropyl)-4,11-dioxo-9-(phenylmethyl)-6-((4-(5-thiazolyl)phenyl)methyl)-, dimethyl ester, (3S-(3R(R),8R,9R,12R*))-	HCID 467949	—

Reaktionsschritte

Under an argon atmosphere, 292 mg of 1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane (Example 2d) and 165 μl (1.5 mmol) of NMM in 4.8 ml of DMF are added to 113 mg of N-methoxycarbonyl-(L)-iso-leucine and 149 mg (0.50 mmol) of TPTU in 2.5 ml of DMF, and the midure is stirred at room temperature for 14 hours and worked up analogously to Example 3, yielding the title compound: m.p: 139-141° C.; TLC: Rf=0.7 (methylene chloride/methanol 10:1); HPLC20-100: tRet=14.6; FAB MS (M+H)+=711.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US06300519B1
Quelldatensatz	uspto-grants-2001_10
ORD ID	ord-d97a97e2c8b34d3cbb97cc8e6b374a9f
Quellennotiz	uspto-grants-2001_10