Triethylamine → (2-{[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester

HRID 1294603ノート

反応式

HRID 1294603 の反応式
Cl.Cl.[NH2:3][CH2:4][C:5]1[C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=[CH:7][N:6]=1.C(N(CC)CC)C.[CH3:25][C:26]([CH3:42])([N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])[CH2:27][C:28](O)=[O:29]>C(Cl)Cl>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:11][C:10]1[C:5]([CH2:4][NH:3][C:28](=[O:29])[CH2:27][C:26]([N:31]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]2=[O:41])([CH3:42])[CH3:25])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:17]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 22038564beta,beta-Dimethyl-1,3dioxo-2-isoindolinepropionic acidHCID 220385702-Aminomethyl-3-(ethoxycarbonylmethoxy)pyridine dihydrochloride

生成物 1

HCID 69158493(2-{[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester収率 62.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-aminomethyl-3-(ethoxycarbonylmethoxy)pyridine dihydrochloride (610 mg, 2.155 mmol), triethylamine (732 μl, 5.258 mmol), N,N-dicyclohexylcarbodiimide (596 mg, 2.892 mmol) and 4-(N,N-diemethylamino)-pyridine (10 mg) in 6 ml of dry methylene chloride is added β,β-dimethyl-1,3-dioxo-2-isoindolinepropionic acid (650 mg, 2.629 mmol) at ambient temperature. The mixture is stirred for 24 hours. The precipitate of dicyclohexyl urea is filtered off. The filtrate is evaporated and the residue is purified via flash chromatography on silica gel using a methylene chloride/methylene chloride-ethanolic ammonia gradient (100 to 97:3) to give 591 mg of (2-{[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester (46%).

後処理

  1. filtrationThe precipitate of dicyclohexyl urea is filtered off
  2. customThe filtrate is evaporated
  3. customthe residue is purified via flash chromatography on silica gel using a methylene chloride/methylene chloride-ethanolic ammonia gradient (100 to 97:3)

出典と根拠

ORDレコード
ord-bd5853c213f4404b852cfa461ffc0e34
出典データセット
uspto-grants-2007_07
特許番号
US07241772B2

反応ノート

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