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*))-

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate	HCID 2733204	—
Reactant	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	—
Reactant	L-Isoleucine, N-(methoxycarbonyl)-	HCID 28378062	—
Solvent	Dimethylformamide	HCID 6228	—
Product	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	—

Reaction Steps

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 mixture 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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06110946
Source dataset	uspto-grants-2000_08
ORD ID	ord-c2e9b475c3e940baa3265dadfe038cc3
Source note	uspto-grants-2000_08