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

HRID 1940966

반응식

HRID 1940966 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

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 flitrate 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).

후처리

  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 flitrate 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

출처 및 근거

ORD 기록
ord-b116d25aeebc42b588904429ff35c998
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700810

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