1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2-trityl-amino-ethyl)-4-ethynyl-benzamide

Participants

Role	Name	HCID	Charge
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-{4-[4-(4-Amino-phenyl)-buta-1,3-diynyl]-benzoylamino}-3-tert-butoxycarbonylamino-propionic acid methyl ester	HCID 57897028	—
Reactant	methyl(2S,3R)-3-hydroxy-2-{[4-(phenylcarbonyl)phenyl]carbonylamino}butanoate	HCID 59697585	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-(2-trityl-amino-ethyl)-4-ethynyl-benzamide	HCID 86595068	97.1%

Reaction Steps

To a solution of 4-ethynylbenzoic acid 1 (292 mg, 2.00 mmol), EDCI (382 mg, 2.00 mmol), and HOBt (270 mg, 2.00 mmol) in DMF (10 mL) was added N-trityl ethylenediamine 2 (810 mg, 2.67 mmol) and DIEA (1.4 mL, 8.0 mmol). The reaction mixture was stirred 24 h, diluted with EtOAc (200 mL), washed with 0.5 M HCl (60 mL), saturated NaHCO3 (2×60 mL), H2O (4×60 mL), dried over MgSO4 and concentrated to give 836 mg (97% yield) of N-(2-trityl-amino-ethyl)-4-ethynyl-benzamide 3 as a white solid, mp 50-51° C. Rf=0.40 (1:1 Hexanes/EtOAc).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08153843B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-50edac234ba84a51af5826db7b41b824
Source note	uspto-grants-2012_04