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

HRID 1739434노트

반응식

HRID 1739434 반응식
[CH2:1]([O:3][C:4](=[O:18])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[NH2:6])[CH3:2].[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][N:28]=1)[C:23](O)=[O:24].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:18])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[NH:6][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][N:28]=[C:20]([Br:19])[CH:21]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 2227012-Bromoisonicotinic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 10060820ethyl (2S)-2-amino-3-(3,4-dimethoxyphenyl)propanoate

생성물 1

HCID 53678990N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester수율 64.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To methylene chloride (120 ml) are added 3-(3,4-dimethoxyphenyl)alanine ethyl ester (12.4 g), 2-bromoisonicotinic acid (10.9 g), 1-hydroxybenzotriazole monohydrate (8.23 g) and 1,3-dicyclohexylcarbodiimide (11.1 g), and the mixture is stirred at room temperature overnight. The insoluble materials are removed by filtration, and the filtrate is concentrated. The residue is purified by silica gel chromatography (solvent; chloroform:acetone=10:1) to give N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester (13.9 g) as an oily product.

후처리

  1. customThe insoluble materials are removed by filtration
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by silica gel chromatography (solvent; chloroform:acetone=10:1)

출처 및 근거

ORD 기록
ord-5fb5678feb824c4c871dd44cada223c3
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965730

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