Hydrochloric Acid → HCID 19101761、化合物

HRID 1974562ノート

反応式

HRID 1974562 の反応式
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].[N+:19]([C:22]1[CH:23]=[C:24]([CH:34]=[CH:35][CH:36]=1)[C:25](OC1C=CC=CC=1)=[O:26])([O-:21])=[O:20].Cl>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]([C:25](=[O:26])[C:24]2[CH:34]=[CH:35][CH:36]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 922304phenyl 3-nitrobenzoateHCID 150472604-(2-Methyl-1H-indol-3-yl)butanoic acid

生成物 1

HCID 19101761HCID 19101761、化合物収率 74.1%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

A solution of 4-(2-methylindol-3-yl)butyric acid (600 mg) in N,N-dimethylformamide (10 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 243 mg) in N,N-dimethylformamide (5 ml) at 20° C. and the mixture was stirred at 20° C. for 1 hour. A solution of phenyl 3-nitrobenzoate (671 mg) in tetrahydrofuran (10 ml) was added to the mixture at -35° C. and the resulting mixture was stirred at the same temperature for 2 hours. The mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the residue was chromatographed on a silica gel (25 g) column with a mixture of hexane and ethyl acetate (10:1 to 1:1) to give 4-[2-methyl-1-(3-nitrobenzoyl)indol-3-yl]butyric acid (749 mg) as yellow crystals.

後処理

  1. stirringthe resulting mixture was stirred at the same temperature for 2 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of solvent
  6. customthe residue was chromatographed on a silica gel (25 g) column with a mixture of hexane and ethyl acetate (10:1 to 1:1)

出典と根拠

ORDレコード
ord-9b1dcc5fc6154995992afce66483e737
出典データセット
uspto-grants-1994_02
特許番号
US05283251

反応ノート

読み込み中…