Diisopropylethylamine → HCID 178427593, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Reactant	Benzyl 2-aminoacetate hydrochloride	HCID 11701227	—
Reactant	HCID 178427598	HCID 178427598	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 178427593	HCID 178427593	83.1%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a suspension of Boc—(D)—Arg(Tos)—OH (1 g, 2.34 mmol) in CH2Cl2 (10 mL) was added DIEA (1 mL) at 0° C. To the clear solution was added Gly—OBn.HCl (0.52 g, 2.58 mmol) and BOP (1.2 g, 2.8 mmol). The solution was stirred for 4 h at 0° C. Solvents were evaporated and residue was dissolved in a mixture of EtOAc (100 mL) and water (20 mL). The organic layer was washed with sat. NaHCO3 (10 mL), water (10 mL), 1 N HCl (10 mL) and sat. NaCl (3×10 mL), dried with MgSO4, filtered and evaporated. The solid residue was purified by column chromatography on silica gel (EtOAc) to give 1.12 g of the title compound as a powder. ES—MS (M+H)+=576.3

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06211154B1
Source dataset	uspto-grants-2001_04
ORD ID	ord-57fa27e35b5f4438a64699e442879d05
Source note	uspto-grants-2001_04