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

HRID 1739434ノート

反応式

HRID 1739434 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5fb5678feb824c4c871dd44cada223c3
出典データセット
uspto-grants-1999_10
特許番号
US05965730

反応ノート

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