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3-(Aminomethyl)-5-methylhexanoic acid → 3-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-5-methyl-hexanoic acid

HRID 1481238
ノート
印刷プレビュー

反応式

HRID 1481238 の反応式
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:25][CH2:26][CH:27]([CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:28][C:29]([OH:31])=[O:30]>C[O-].[Na+].CO>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:25][CH2:26][CH:27]([CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:28][C:29]([OH:31])=[O:30])=[O:4])[N:6]=1)#[N:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 47151693-(Aminomethyl)-5-methylhexanoic acidHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

生成物 1

HCID 898128883-{[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-methyl}-5-methyl-hexanoic acid収率 48.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 10942334Sodium Methoxide
溶媒

実験手順

A mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.16 mmole) and 3-(aminomethyl)-5-methylhexanoic acid (249 mg, 1.6 mmole, AK Scientific) in 0.5 M sodium methoxide in methanol (2.5 ml) was refluxed for two days before it was cooled to room temperature, concentrated and dissolved in water, extracted with dichloromethane. The remaining aqueous layer was acidified with 1N hydrochloric chloride, extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by flash column chromatography on silica gel with a gradient of dichloromethane and ethyl acetate to give the title compound as a white solid (35 mg). LC-MS ESI+: 448 (M+1)+; ESI−: 446 (M-1)−.

後処理

  1. temperaturewas refluxed for two days before it
  2. concentrationconcentrated
  3. dissolutiondissolved in water
  4. extractionextracted with dichloromethane
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by flash column chromatography on silica gel with a gradient of dichloromethane and ethyl acetate

出典と根拠

ORDレコード
ord-22612ae01ef14d99a7f75aa4295769d4
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409892B2

反応ノート

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