Water → Di-tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoyl)amino]-1,3-propanediyl}biscarbamate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	tert-butyl N-(2-amino-3-{[(tert-butoxy)carbonyl]amino}propyl)carbamate	HCID 15186003	—
Reactant	3-{[1-Methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoic acid	HCID 21904581	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Di-tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoyl)amino]-1,3-propanediyl}biscarbamate	HCID 86760458	72.1%

Reaction Steps

A mixture of 3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoic acid (600 mg), di-tert-butyl (2-amino-1,3-propanediyl)biscarbamate (434 mg) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (522 mg) in tetrahydrofuran (12 ml) and methylene chloride (6 ml) was stirred overnight at room temperature. Water was added and the whole mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave a residue, which was triturated with diisopropyl ether-ethyl acetate (2:1) to give di-tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoyl)amino]-1,3-propanediyl}biscarbamate (699 mg) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07192943B2
Source dataset	uspto-grants-2007_03
ORD ID	ord-38bc5a0323cd4b3cbe293dd33a169905
Source note	uspto-grants-2007_03