Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 745741Notes

Reaction equation

HRID 745741 reaction equation
C(N)CCCCCCCCCCCCCCCC.[CH:19]1([N:25]=[C:26]=[N:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.N(C(OC(C)(C)C)=O)(CC(O)=[O:38])C>C(Cl)(Cl)Cl>[C:26]([NH:25][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)([NH:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:38]

Participants

5

Reactant 3

HCID 10868Dicyclohexylcarbodiimide2×HCID 15791HeptadecylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

C17BocSar1 : the product C17BocSar1 is obtained by coupling heptadecylamine with BocSar1 in the presence of dicyclohexylcarbodiimide (DCCI). 3.78 g (0.02 mole) of BocSar and 2.06 g (0.01 mole) of DCCI are mixed cold (at 0° C.) in 100 ml of chloroform. A copious precipitate of dicyclohexylurea (DCU) is formed. The mixture is left for 30 minutes at 0° C., with agitation, and 2.55 g (0.01 mole) of heptadecylamine are added. The reaction is left to proceed for 20 hours. The precipitate is filtered off and washed, the filtrate is recovered, the chloroform is evaporated off, the residue is taken up in 50 ml of THF, the mixture is cooled to 0° C. and filtered to remove the maximum amount of dicyclohexylurea, and the precipitate is washed with the minimum amount of cold THF.

Workup

  1. customC17BocSar1 : the product C17BocSar1 is obtained

Sources & evidence

ORD record
ord-65d3e44c71d54ad39804d2efbd1b4efc
Source dataset
uspto-grants-1986_07
Patent number
US04600526

Reaction notes

Loading…