Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1380285Notes

Reaction equation

HRID 1380285 reaction equation
[OH:1]CC(C1N=C(NC(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)SC=1)C(O)=O.[CH:32]1([N:38]=[C:39]=[N:40][CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>O1CCCC1>[CH:41]1([NH:40][C:39]([NH:38][CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)=[O:1])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 136050753-Hydroxy-2-(2-tritylaminothiazol-4-yl)propionic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of anhydrous tetrahydrofuran were dissolved 430 mg (1 millimole) of 3-hydroxy-2-(2-tritylaminothiazol-4-yl)propionic acid, 510 mg (1 millimole) of 7β-amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-Δ3 -cephem-4-carboxylic acid benzhydryl ester, and after adding thereto 206 mg (1 millimole) of N,N'-dicyclohexylcarbodiimide, the mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure and then 40 ml of ethyl acetate was added to the residue. Insoluble N,N'-dicyclohexylurea formed was filtered off and the filtrate was washed with a diluted aqueous acid solution and an aqueous solution of sodium hydrogencarbonate and dried by anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then, the residue was treated with ether to form a powder, which was recovered by filtration, and washed with water to provide 720 mg of 7β-[3-hydroxy-2-(2-tritylaminothiazol-4-yl)propionamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-Δ3 -cephem-4-carboxylic acid benzhydryl ester.

Workup

  1. additionafter adding
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. addition40 ml of ethyl acetate was added to the residue

Sources & evidence

ORD record
ord-ec761d888e3a426087d3131a786bc9dd
Source dataset
uspto-grants-1986_04
Patent number
US04581353

Reaction notes

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