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

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1-[4-(Thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-valyl)amino6-phenyl-2-azahexane	HCID 10697413	—
Reactant	L-Isoleucine, N-(methoxycarbonyl)-	HCID 28378062	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2,5,6,10,13-Pentaazatetradecanedioic acid, 8-hydroxy-12-(1-methylethyl)-3-(1-methylpropyl)-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-thiazolyl)phenyl)methyl)-, dimethyl ester, (3S-(3R(R),8R,9R,12R*))-	HCID 467963	—

Reaction Steps

Analogously to Example 7, 106 mg (0.56 mmol) of N-methoxycarbonyl-(L)-iso-leucine, 201 mg (1.05 mmol) of EDC and 95 mg (0.7 mmol) of HOBT in 4.6 ml of DMF and 293 μl (2.1 mmol) of TEA are reacted with 0.35 mmol of 1-[4-(thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-valyl)amino-6-phenyl-2-azahexane to form the title compound: m.p: 227-229° C.; HPLC20-100 : tRet =14.5; 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-75ee7d4bdff54fa0931d647c5aaa4246
Source note	uspto-grants-2000_08