Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1439255Notes

Reaction equation

HRID 1439255 reaction equation
[OH:1]N1C(=O)CCC1=O.[CH:9]1([N:15]=[C:16]=[N:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>O1CCCC1>[CH:18]1([NH:17][C:16]([NH:15][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)=[O:1])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide2×

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The half-ester of the formula (VI) may be converted into an "activated" ester prior to reaction with the 7-(α-aminoarylacetamido)-4-carboxy-Δ3 -cephem derivative using the preferred reagent N-hydroxysuccinimide in the presence of a dehydrating agent such as dicyclohexylcarbodiimide. The "activated" ester product of the formula: ##STR5## is conveniently then reacted with the Δ3 -cephem derivative in the reaction solution in which it has been formed, without isolation. In a typical procedure, a solution of the half-ester, N-hydroxysuccinimide and dehydrating agent in a reaction-inert organic solvent, e.g. tetrahydrofuran, is stirred for several hours at room temperature, after which the solid N,N'-dicyclohexylurea formed in the reaction may be removed, e.g. by filtration. To the solution containing the "activated" ester is then added a solution of the Δ3 -cephem derivative, and reaction generally goes substantially to completion in the presence of a tertiary amine or inorganic base, as hereinbefore examplified and preferably with stirring during a period from 1 to 12 hours at room temperature. The solvent may then be removed, e.g. by evaporation in vacuo, and the residue dissolved in water, the aqueous solution then being acidified, extracted with a water-immiscible organic solvent, e.g. ethyl acetate, and the organic phase subjected to a similar procedure to that described in Method (1) for the isolation and purification of the product.

Workup

  1. customhas been formed, without isolation

Sources & evidence

ORD record
ord-de8f25644d1844bab0fb29269711a6cd
Source dataset
uspto-grants-1977_11
Patent number
US04058610

Reaction notes

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