1,2-Dichloroethane → 2,5,6,10,13-Pentaazatetradecanedioic acid, 8-hydroxy-3,12-bis(1-methylethyl)-4,11-dioxo-9-(phenylmethyl)-6-((4-(5-thiazolyl)phenyl)methyl)-, 1-ethyl 14-methyl ester, (3S-(3R,8R,9R,12R))-

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1-[4-(Thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-valyl)amino-6-phenyl-2-azahexane	HCID 10768426	—
Reactant	N-Carbethoxy-L-valine	HCID 13221302	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2,5,6,10,13-Pentaazatetradecanedioic acid, 8-hydroxy-3,12-bis(1-methylethyl)-4,11-dioxo-9-(phenylmethyl)-6-((4-(5-thiazolyl)phenyl)methyl)-, 1-ethyl 14-methyl ester, (3S-(3R,8R,9R,12R))-	HCID 467953	—

Reaction Steps

Analogously to Example 7, 213 mg (1.13 mmol) of N-ethoxycarbonyl-(L)-valine, 431 mg (2.25 mmol) of EDC and 304 mg (2.25 mmol) of HOBT in 18 ml of DMF and 627 μl (4.5 mmol) of TEA are reacted with 0.75 mmol of 1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-valyl)amino-6-phenyl-2-azahexane (Example 7b) to form the title compound: m.p: 243-244° C.; HPLC20-100 : tRet =14.0; FAB MS (M+H)+ =697.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06110946
Source dataset	uspto-grants-2000_08
ORD ID	ord-4978bd3090364e9eb6ab2d08c6606cbb
Source note	uspto-grants-2000_08