Methanol → 5-acetamido-1H-indole-2-carboxylic Acid

HRID 1874829ノート

反応式

HRID 1874829 の反応式
[OH-].[Li+].[C:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](C(OCCC(C)(C)C)=O)[C:11]([C:25]([O-:27])=[O:26])=[CH:10]2)(=[O:5])[CH3:4].CO.O>C1COCC1>[C:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:25]([OH:27])=[O:26])=[CH:10]2)(=[O:5])[CH3:4]

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 867616451-(1,1-dimethylethyl)2-ethyl 5-(acetylamino)-1H-indole-1,2-dicarboxylate

生成物 1

HCID 107751705-acetamido-1H-indole-2-carboxylic Acid収率 43%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

Lithium hydroxide (0.028 g, 1.184 mmol) was added to a solution of 1-(1,1-dimethylethyl)2-ethyl 5-(acetylamino)-1H-indole-1,2-dicarboxylate (0.041 g, 0.118 mmol) in THF:MeOH:water/3:1:1. The reaction mixture was heated at 50° C. for 1 h. The solvent was evaporated. The residue was dissolved in water, acidified with 6N aqueous HCl and extracted with dichloromethane. A solid formed in the aqueous layer which was collected by filtration and dried to give the title compound (0.011 g, 43%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.85 (s, 1H), 11.63 (s, 1H), 9.79 (s, 1H), 7.97 (s, 1H), 7.22-7.38 (m, 2H), 7.01 (s, 1H), 2.01 (s, 3H). MS: m/z 219 (M+1).

後処理

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. customA solid formed in the aqueous layer which
  5. filtrationwas collected by filtration
  6. customdried

出典と根拠

ORDレコード
ord-1c71022b3f0046cc8e2113237c7c4923
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

読み込み中…