Dicyclohexylcarbodiimide → N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester

HRID 1739436노트

반응식

HRID 1739436 반응식
Cl.[CH2:2]([O:4][C:5](=[O:19])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[NH2:7])[CH3:3].[Br:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24](O)=[O:25].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(N(CC)CC)C>[CH2:2]([O:4][C:5](=[O:19])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[NH:7][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][N:29]=[C:21]([Br:20])[CH:22]=1)[CH3:3]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 2227012-Bromoisonicotinic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 186595423,4-dimethoxy-L-phenylalanine ethyl ester-hydrochloride

생성물 1

HCID 53678990N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester수율 93.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

3-(3,4-Dimethoxyphenyl)-L-alanine ethyl ester hydrochloride (66 g), triethylamine (33.3 ml), 2-bromoisonicotinic acid (50.6 g), 1-hydroxybenzotriazole monohydrate (38.4 g) and 1,3-dicyclohexylcarbodiimide (51.7 g) are added to methylene chloride (660 ml), and the mixture is stirred at room temperature for four hours. The reaction mixture is washed, dried, and concentrated. The residue is purified by silica gel chromatography (solvent; chloroform:acetone=10:1) to give N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)-L-alanine ethyl ester (93.5 g).

후처리

  1. washThe reaction mixture is washed
  2. customdried
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel chromatography (solvent; chloroform:acetone=10:1)

출처 및 근거

ORD 기록
ord-4c1f7d599ba24299974f5cebb23668f3
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965730

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