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 (2 mL) and BOP (2.5 g, 5.6 mmol). The solution was stirred at 0° C. for 10 h. DMF was evaporated in vacuo. 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, washed with cold EtOAc (10 mL) and dried to give Boc—Arg(Tos)—N(Me)OMe (1.5 g, 70% yield). FAB—MS (M+H)+=472

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06211154B1
Source dataset	uspto-grants-2001_04
ORD ID	ord-8a687ebb3f5f4b44b0bb57cc1571528d
Source note	uspto-grants-2001_04