D-Tryptophan → HCID 22855681, compound

Participants

Role	Name	HCID	Charge
Reactant	D-Tryptophan	HCID 9060	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(2S)-2-(azepane-1-carbonylamino)-4-methylpentanoic acid	HCID 7530182	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 22855681	HCID 22855681	—

Reaction Steps

The compound obtained in (2) (1.08 g) and DTrp-Ome.Hcl (1.02 g) were dissolved in DMF (10 ml), and TEA (0.57 ml), HOBT.H2O (613 mg) and EDCI.HCl (805 mg) were added at 0°~5° C. The reaction mixture was stirred at 0°~5° C. for 1.5 h and at room temperature for 4 h. Water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with 1N HCl and sat. NaHCO3, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by MPLC (Merck, LiChroprep Si 60) with dichloromethane/methanol=30/1 for elution to give the product (1.55 g) as a colorless powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05444152
Source dataset	uspto-grants-1995_08
ORD ID	ord-0edaaef06f1a442db1b951300203a222
Source note	uspto-grants-1995_08