1,2-Dichloroethane → N2-(tert-butoxycarbonyl)-N1-[(1S)-1-({[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]amino}carbonyl)propyl]-4-methyl-D-leucinamide

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	Triethylamine	HCID 8471	—
Reactant	HOAt	HCID 181649	—
Reactant	(R)-2-((tert-Butoxycarbonyl)amino)-4,4-dimethylpentanoic acid	HCID 7021114	—
Reactant	(2S)-2-amino-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]butanamide	HCID 69656288	—
Solvent	Methanol	HCID 887	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N2-(tert-butoxycarbonyl)-N1-[(1S)-1-({[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]amino}carbonyl)propyl]-4-methyl-D-leucinamide	HCID 86591819	—

Reaction Steps

A mixture of Boc-D-t-butyl-alanine (49 mg, 0.20 mmol), (2S)-2-amino-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]butanamide (66 mg, 0.20 mg), HOAt (27 mg, 0.20 mmol), EDC (57 mg, 0.30 mmol), and Et3N (28 μL, 0.20 mmol) in 1.0 mL of DMF was stirred at rt overnight. A small amount of MeOH was used to aid in dissolution. Solvent was removed in vacuo to give the title compound, which was carried on directly to deprotection. LCMS (M+H): 521.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07144899B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-aefaf23bf3594c7fa2b416bf9873282f
Source note	uspto-grants-2006_12