N,N'-Dicyclohexylcarbodiimide

dicyclohexylcarbodiimideN'',''N′''-dicyclohexylcarbodiimideDCCDCCDN'',''N ''-dicyclohexylcarbodiimideN'',''N'''-DicyclohexylcarbodiimideN'',''N''-dicyclohexylcarbodiimideN,N'''-dicyclohexylcarbodiimide
N,N′-Dicyclohexylcarbodiimide (DCC or DCCD) is an organic compound with the chemical formula (C 6 H 11 N) 2 C.wikipedia
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Peptide synthesis

solid phase peptide synthesissynthetic peptidesolid-phase peptide synthesis
Its primary use is to couple amino acids during artificial peptide synthesis.
Carbodiimides such as dicyclohexylcarbodiimide (DCC) and diisopropylcarbodiimide (DIC) are frequently used for amide bond formation.

Steglich esterification

In the Steglich esterification, alcohols, including even some tertiary alcohols, can be esterified using a carboxylic acid in the presence of DCC and a catalytic amount of DMAP.
The Steglich esterification is a variation of an esterfication with dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst.

Dicyclohexylurea

N,N'-dicyclohexyl urea
DCC has also been prepared from dicyclohexylurea using a phase transfer catalyst by Jaszay et al. The disubstituted urea, arenesulfonyl chloride, and potassium carbonate react in toluene in the presence of benzyl triethylammonium chloride to give DCC in 50% yield.
It is the byproduct of the reaction of dicyclohexylcarbodiimide with amines or alcohols.

Carbodiimide

carbodiimides
* Carbodiimide
A well known carbodiimide is dicyclohexylcarbodiimide, which is used in peptide synthesis.

Pfitzner–Moffatt oxidation

Moffatt oxidationPfitzner-Moffatt oxidationMoffatt
In combination with dimethyl sulfoxide (DMSO), DCC effects the so-called Pfitzner-Moffatt oxidation.
The oxidant is a combination of dimethyl sulfoxide (DMSO) and dicyclohexylcarbodiimide (DCC).

Formic acid

formicformateHCO 2 H
An unstable formic anhydride, H(C=O)−O−(C=O)H, can be obtained by dehydration of formic acid with N,N′-dicyclohexylcarbodiimide in ether at low temperature.

ATP synthase

ATP synthesisATPATPase
DCC is a classical inhibitor of ATP synthase.
Some of the most commonly used ATP synthase inhibitors are oligomycin and DCCD.

Organic compound

syntheticorganicorganic compounds
N,N′-Dicyclohexylcarbodiimide (DCC or DCCD) is an organic compound with the chemical formula (C 6 H 11 N) 2 C. It is a waxy white solid with a sweet odor.

Amino acid

amino acidsresiduesresidue
Its primary use is to couple amino acids during artificial peptide synthesis.

Dichloromethane

methylene chloridemethylene dichlorideDCM
It is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.

Tetrahydrofuran

THFOxolane1,4-Epoxybutane
It is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.

Acetonitrile

CH 3 CNmethyl cyanideMeCN
It is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.

Dimethylformamide

DMFdimethyl formamideN,N-dimethylformamide
It is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.

Properties of water

waterH 2 Owater molecule
It is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.

Allene

allenesallenoallenolate
The C-N=C=N-C core of carbodiimides (N=C=N) is linear, being related to the structure of allene.

Molecular symmetry

symmetrypoint grouporbital symmetry
The molecule has idealized C 2 symmetry.

Nuclear magnetic resonance

NMRmagnetic resonanceNuclear Magnetic Resonance (NMR)
The 15 N NMR spectrum shows a characteristic shift of 275 ppm upfield of nitric acid and the 13 C NMR spectrum features a peak at about 139 ppm downfield from TMS.

Palladium(II) acetate

palladium acetatepalladium complexpalladium(II)acetate
Of the several syntheses of DCC, Pri-Bara et al. use palladium acetate, iodine, and oxygen to couple cyclohexyl amine and cyclohexyl isocyanide.

Isocyanide

isonitrileisonitrilesIsocyanides
Of the several syntheses of DCC, Pri-Bara et al. use palladium acetate, iodine, and oxygen to couple cyclohexyl amine and cyclohexyl isocyanide.

Isocyanate

isocyanatesdiisocyanatepolyisocyanate
Tang et al. condense two isocyanates using the catalyst OP(MeNCH 2 CH 2 ) 3 N in yields of 92%:

Phase-transfer catalyst

phase transfer catalystphase-transfer catalysisphase transfer catalysis
DCC has also been prepared from dicyclohexylurea using a phase transfer catalyst by Jaszay et al. The disubstituted urea, arenesulfonyl chloride, and potassium carbonate react in toluene in the presence of benzyl triethylammonium chloride to give DCC in 50% yield.

Potassium carbonate

pearlashK 2 CO 3 potassium
DCC has also been prepared from dicyclohexylurea using a phase transfer catalyst by Jaszay et al. The disubstituted urea, arenesulfonyl chloride, and potassium carbonate react in toluene in the presence of benzyl triethylammonium chloride to give DCC in 50% yield.

Amide

amidesamidationamidated
DCC is a dehydrating agent for the preparation of amides, ketones, nitriles.

Ketone

ketonesketoketo group
DCC is a dehydrating agent for the preparation of amides, ketones, nitriles.

Nitrile

nitrilesnitrile oxidenitrile group
DCC is a dehydrating agent for the preparation of amides, ketones, nitriles.