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 t (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	US06166004
Source dataset	uspto-grants-2000_12
ORD ID	ord-33cce6669f0541ad9b95735369bd7b11
Source note	uspto-grants-2000_12