Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 178502742, compound

Participants

Role	Name	HCID	Charge
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
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. was added MeNHOMe·HCl (1 g, 10.3 mmol), DIEA (6 mL) and BOP (2.5 g, 5.6 mmol). The solution was stirred at 0° C. for 10 hours. DMF was evaporated by vacuum. The oily residue was dissolved in EtOAc (200 mL) and water (20 mL). The organic layer was washed with sat. NaHCO3, water (20 mL), 1 M HCl (10 mL) and sat. NaCl (2×20 mL). The organic layer was dried over MgSO4, filtered and evaporated to give a suspension. The suspension was filtered, and the solid was washed with cold EtOAc (10 mL) and dried to give Boc-Arg(Tos)-N(Me)OMe, shown above, (1.5 g, 70% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06133256
Source dataset	uspto-grants-2000_10
ORD ID	ord-1269af789f834684992516fd2712e1d5
Source note	uspto-grants-2000_10