Dichloromethane → {1-[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-2-yl]-ethyl}-carbamic Acid Tert-Butyl Ester

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	2-amino-N-(4-ethoxyphenyl)benzamide	HCID 750179	—
Reactant	(2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid	HCID 2724627	—
Product	{1-[1-(4-Ethoxy-phenyl)-1H-benzoimidazol-2-yl]-ethyl}-carbamic Acid Tert-Butyl Ester	HCID 23401405	—

Reaction Steps

To a mixture of compound XX (7.68 g, 30 mmol) and N-(9-fluorenylmethyloxycarbonyl)-D-alanine (10.26 g, 33 mmol) in CH2Cl2 (150 mL), was added EDAC (8.63 g, 45 mmol) and HOBt (1.38 g, 9 mmol). After stirring at room temperature overnight, the resulting solid was filtered and washed with ethyl ether to yield compound XXI (14.50 g). 1H NMR (CDCl3) 1.37 (t, 3H, J=7.0 Hz), 1.48 (d, 3H, J=7.2 Hz), 3.89 (m, 2H), 4.26 (m, 2H), 4.45 (m, 2H), 5.50 (m, 1H), 6.76 (m, 2H), 7.17 (t, 1H, J=7.3 Hz), 7.25-7.76 (m, 12H), 8.62 (d, 1H, J=8.8 Hz), 11.43 (s, 1H).MS(ESI+) 550.3 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06794379B2
Source dataset	uspto-grants-2004_09
ORD ID	ord-bab147d48e9d4f81a47d22b067a04ce2
Source note	uspto-grants-2004_09