Dicyclohexylcarbodiimide → BOC-Phe-(D)Trp-Lys(Z)-OMe

https://huagongshe.com/reaction/1903340

Participants

Role	Name	HCID	Charge
Reactant	Dicyclohexylcarbodiimide	HCID 10868	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-	HCID 77857	—
Reactant	H-(D)Trp-Lys(Z)-OMe hydrochloride	HCID 13391306	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Triethylamine	HCID 8471	—
Product	BOC-Phe-(D)Trp-Lys(Z)-OMe	HCID 13391308	—

Reaction Conditions

Temperature	-20 °C

Reaction Steps

9.5 ml NEt3, 13 g HOBT and 17 g BOC-Phe-OH are added to 35 g H-(D)Trp-Lys(Z)-OMe hydrochloride in 350 ml DMF. The solution is cooled to -20° C. and 14.5 g DCCI dissolved in 50 ml DMF are added. The reaction mixture is stirred for ca. 18 hrs. at 0° C. and then for 1 day at room temperature. The precipitated dicyclohexyl-urea is filtered off and the filtrate is concentrated, diluted with methanol and H2O added until precipitation occurs. After filtration the residue is washed with MeOH/H2O (4:1) and dried to yield the title compound:

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04435385
Source dataset	uspto-grants-1984_03
ORD ID	ord-b6b161e30d1a491bb9b5bd50b1085533
Source note	uspto-grants-1984_03