1-Hydroxybenzotriazole → Boc-Leu-DTrp-OMe

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate hydrochloride	HCID 11448200	—
Reactant	N-Boc-L-Leucine Hydrate	HCID 12373896	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	Boc-Leu-DTrp-OMe	HCID 14504288	96.5%

Reaction Steps

To a suspension of Boc-Leu-OH.H2O (0.997 g) and DTrp-OMe.HCl (1.021 g) in dichloromethane (10 ml) were added TEA (0.6 ml) and HOBT.H2O (0.615 g) under argon. EDCI.HCl (0.769 g) was added to the mixture at 0°~5° C. The resulting reaction mixture was stirred at room temperature for 16 h, washed successively with water, 10% aq. citric acid, sat. NaHCO3 and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was triturated with hexane to give the product (1.665 g). FAB-MS(m/e, (C23H33N3O5 +H)+):432

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05470833
Source dataset	uspto-grants-1995_11
ORD ID	ord-29c5aadcc04c4e48af44822bf868f680
Source note	uspto-grants-1995_11