Hydrochloric Acid → Ethyl 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate

HRID 239948ノート

反応式

HRID 239948 の反応式
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([NH:18][C:19]3[C:29]([CH3:30])=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][C:20]=3[CH3:31])=[O:17])[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC(C)=O.O.[OH-].[Na+]>[CH3:31][C:20]1[CH:21]=[C:22]([CH:28]=[C:29]([CH3:30])[C:19]=1[NH:18][C:16](=[O:17])[C:15]1[CH:32]=[C:11]([N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[CH:12]=[CH:13][C:14]=1[CH3:33])[C:23]([O:25][CH2:26][CH3:27])=[O:24]

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 86707334Ethyl 4-[[5-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoate

生成物 1

HCID 86707335Ethyl 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate収率 61%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
60 °C

実験手順

To a solution of ethyl 4-[[5-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoate (205 mg, 452.99 μmoles) in acetone (5 ml) is added a mixture of 5M HCl (1 mL) in H2O (1 mL) and heated to 60° C. After 12 hours, the mixture is cooled to ambient temperature, diluted with 2M NaOH to pH 6 and extracted with ethyl acetate. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using 0-40% ethyl acetate in hexane to afford the title compound as an off-white foam (0.11 g, 61%). Mass spectrum (m/z): 409.2 (M+1).

後処理

  1. temperaturethe mixture is cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash chromatography (silica gel)

出典と根拠

ORDレコード
ord-30dd5f52bdb74d6d8d520f1790e4019a
出典データセット
uspto-grants-2014_02
特許番号
US08642768B2

反応ノート

読み込み中…