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

HRID 1739436ノート

反応式

HRID 1739436 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-4c1f7d599ba24299974f5cebb23668f3
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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