1,2-Dichloroethane → (1-{1-Cyclohexyl-2-[4-cyclopropanecarbonyl-6-(1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethylcarbamoyl}-ethyl) methyl-carbamic benzyl ester

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Z-N-Me-Ala-OH	HCID 7016365	—
Reactant	4-(2-Amino-2-cyclohexyl-acetyl)-1-cyclopropanecarbonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide	HCID 67281363	—
Solvent	Dichloromethane	HCID 6344	—
Product	(1-{1-Cyclohexyl-2-[4-cyclopropanecarbonyl-6-(1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethylcarbamoyl}-ethyl) methyl-carbamic benzyl ester	HCID 67282642	95.2%

Reaction Steps

A solution of 47 (330 mg, 0.67 mmol) in DCM (10 mL) was cooled to 0° C. and treated with Cbz-N(Me)Ala-OH (159 mg, 0.67 mmol), EDC (154 mg, 0.80 mmol), HOBt (109 mg, 0.80 mmol) and DIPEA (0.36 mL, 2.08 mmol), respectively. After 18 h, the solution was diluted with DCM, washed successively with 1M HCl, saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 48 (454 mg) as a white foam that was used without further purification. Mass spectrum, m/z [712.9] (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08481495B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-54d1943492004668a2bff5e9cedb9c4c
Source note	uspto-grants-2013_07