Diisopropylethylamine → HCID 178502742, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methylphenyl)sulfonyl]amino]methyl]-	HCID 83767	—
Reactant	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178502742	HCID 178502742	70%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a suspension of Boc-Arg(Tos)--OH (2 g, 4.7 mmol) in DMF (20 mL) at 0° C. is added MeNHOMeHCl (1 g, 10.3 mmol), DIEA (6 mL) and BOP (2.5 g, 5.6 mmol). The solution is stirred at 0° C. for 10 hours. DMF is evaporated by vacuum. The oily residue is dissolved in EtOAc (200 mL) and water (20 mL). The organic layer is washed with sat. NaHCO3, water (20 mL), 1 M HCl (10 mL) and sat. NaCl (2×20 mL). The organic layer is dried over MgSO4, filtered and evaporated to give a suspension. The suspension is filtered, washed with cold EtOAc (10 mL) and dried to give Boc-Arg(Tos)-N(Me)OMe, shown above, (1.5 g, 70 % yield). FAB-MS (M+H)+=472

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06063794
Source dataset	uspto-grants-2000_05
ORD ID	ord-7bd4fafd470e44a5bd8ee73be2991b11
Source note	uspto-grants-2000_05