Dicyclohexylcarbodiimide → HCID 178445956, compound

Participants

Role	Name	HCID	Charge
Reactant	Dicyclohexylcarbodiimide	HCID 10868	—
Reactant	3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione	HCID 89529	—
Reactant	L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)	HCID 6451312	—
Reactant	HCID 131710603	HCID 131710603	—
Reactant	HCID 178512168	HCID 178512168	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178445956	HCID 178445956	—

Reaction Conditions

Temperature	-10 °C

Reaction Steps

In 5 ml. of DMF was dissolved 275 mg. of H-Leu-OBzl-p-toluenesulfonate and the solution was neutralized with 0.9 ml. of 10 % N-ethylmorpholine-DMF. Under cooling at -10° C, 670 mg. of Z-β-Ala-Arg(NO2)-Gly-Phe-Phe-Tyr-OH, 251 mg. of HONB and 289 mg. of DCC were added. The mixture was stirred for 12 hours and the formed DC-urea was filtered off. The DMF was distilled off under reduced pressure and 30 ml. of water was added to the residue. The resulting precipitate was collected by filtration, washed with hot methanol and dried. Yield 703 mg. (87.9 %) melting point: 178- 181° C; α!D23 -15.0°(c=1.02 %, DMF)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04073890
Source dataset	uspto-grants-1978_02
ORD ID	ord-9513be9ed3db40c3ad219404962f9d2e
Source note	uspto-grants-1978_02