Hydrochloric Acid → HCID 71737074、化合物

HRID 1481058ノート

反応式

HRID 1481058 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].Cl.[NH2:26][C@@H:27]([CH:32]([CH3:34])[CH3:33])[CH2:28][C:29]([OH:31])=[O:30].C[O-].[Na+].Cl>COCCO>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[CH2:28][C:29]([OH:31])=[O:30])=[O:4])[N:6]=1)#[N:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 2761557L-beta-Homovaline hydrochlorideHCID 10942334Sodium MethoxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

生成物 1

HCID 71737074HCID 71737074、化合物収率 13.4%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

反応条件

温度
130 °C

実験手順

A mixture of 1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.16 mmole), (R)-3-amino-4-methylpentanoic acid hydrochloride (52 mg, 0.31 mmole) (Chem-Impex International Inc., Wood Dale Ill.), and sodium methoxide (25 mg, 0.46 mmole) in 2-methoxyethanol was stirred at 130° C. for two hours before it was cooled to room temperature and acidified with 1 N HCl. The mixture was partitioned between dichloromethane and water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of 1% acetic acid, ethyl acetate and hexanes to give the title compound as a yellow solid (9 mg): MS: (+) m/z 420.06 (M+1), (−) m/z 418.02 (M−1).

後処理

  1. temperaturewas cooled to room temperature
  2. customThe mixture was partitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel with a gradient of 1% acetic acid, ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-9c33426826a14dd19cea39ca411c04e7
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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