Dicyclohexylcarbodiimide → N-[2-(4-fluorobenzoyl)benzoyl]-N-methylglycine ethyl ester

HRID 374999

Reaction equation

HRID 374999 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH2:45]([O:47][C:48](=[O:52])[CH2:49][NH:50][CH3:51])[CH3:46]>C(N(CC)CC)C.C1COCC1>[CH2:45]([O:47][C:48](=[O:52])[CH2:49][N:50]([C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=1[C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:18][CH:17]=1)[CH3:51])[CH3:46]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 820992-(4-Fluorobenzoyl)benzoic acidHCID 171173Ethyl N-methylaminoacetate hydrochloride

Product 1

HCID 21463059N-[2-(4-fluorobenzoyl)benzoyl]-N-methylglycine ethyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-(4-fluorobenzoyl)benzoic acid (3.00 g), 1-hydroxybenzotriazole (2.07 g), 1,3-dicyclohexylcarbodiimide (3.00 g) and anhydrous THF (50 ml) was stirred at room temperature for 1 hour. To this mixture were added N-methylglycine ethyl ester hydrochloride (2.84 g) and triethylamine (2.58 ml), followed by stirring at room temperature for 16 hours and with heating and refluxing for 4 hours. After the solvent was distilled off, ethyl acetate was added to the residue, and the insoluble crystals were separated by filtration. The filtrate was washed successively with water, aqueous sodium hydrogen carbonate, water, dilute hydrochloric acid and water and then dried, after which the solvent was distilled off, to yield N-[2-(4-fluorobenzoyl)benzoyl]-N-methylglycine ethyl ester as a colorless oily substance (4.2 g).

Workup

  1. stirringby stirring at room temperature for 16 hours
  2. temperaturewith heating
  3. temperaturerefluxing for 4 hours
  4. distillationAfter the solvent was distilled off
  5. additionethyl acetate was added to the residue
  6. customthe insoluble crystals were separated by filtration
  7. washThe filtrate was washed successively with water, aqueous sodium hydrogen carbonate, water, dilute hydrochloric acid and water
  8. customdried
  9. distillationafter which the solvent was distilled off

Sources & evidence

ORD record
ord-0ae52ed9dc254deaa9ffde3f0b954e69
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Linked notes

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