Dimethylformamide → N,N'-Dicyclohexylurea

HRID 1740770Notes

Reaction equation

HRID 1740770 reaction equation
CN(C1C=CC=CN=1)C.[CH:10]1([N:16]=[C:17]=[N:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CN(C)C=[O:28]>>[CH:19]1([NH:18][C:17](=[O:28])[NH:16][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 218852-Dimethylaminopyridine

Product 1

HCID 4277N,N'-Dicyclohexylurea

Conditions

Temperature
0 °C

Procedure

An equimolecular mixture (10-2M) of L-N-Boc-NG -nitroarginine and N-B-hydroxyethyl morpholine is dissolved in 30 ml of anhydrous dimethyl formamide (DMF), then 3×10-3M of dimethylaminopyridine (DMAP) is added. The solution is cooled to 0 degrees C. and 10-2M of dicyclohexyl carbodiimide (DDC) is added. It is stirred at 0 degrees C. for 10 minutes, then the stirring is continued at room temperature for 24 hours. The precipitate of dicyclohexyl urea formed is filtered and the solvent eliminated. The residue is recovered by ethyl acetate, then washed once with water and once with saturated NaCl. The elimination of the solvent leaves a viscous product which is chromatographed on a silica column (eluant CHCl3/MeOH9595 then 90:10); the compound (4) is obtained in the form of an oil which crystalizes.

Workup

  1. waitthe stirring is continued at room temperature for 24 hours

Sources & evidence

ORD record
ord-1ea00f151bc24a49a246b1dea20464f9
Source dataset
uspto-grants-1999_10
Patent number
US05972940

Reaction notes

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