Acetic Acid → 5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid

HRID 25660

反応式

HRID 25660 の反応式
[C:1]([O:5][C:6](=[O:16])[N:7]([CH3:15])[CH:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br-].[C:18]([CH2:21][CH2:22][CH2:23][CH2:24][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:20])=[O:19].[H-].[Na+].CC(O)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:7]([CH3:15])[CH:8]1[CH2:13][CH2:12][C:11](=[CH:24][CH2:23][CH2:22][CH2:21][C:18]([OH:20])=[O:19])[CH2:10][CH2:9]1)=[O:16])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 24820328tert-butyl N-methyl-N-(4-oxocyclohexyl)carbamate

生成物 1

HCID 225676825-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid収率 85.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

5 g (21.99 mmol) Methyl-(4-oxo-cyclohexyl)-carbamic acid tert-butyl ester and 12.68 g (28.59 mmol) (4-Carboxy-butyl)-triphenyl-phosphonium bromide were dispended in 50 ml DMF. In small portions 2.49 g (57.2 mmol, 55%) NaH were added and the slurry was diluted by adding 50 ml DMF. The mixture was stirred at RT over night, 10 ml AcOH were added and the solvent was evaporated under reduced pressure. The residue was dissolved in ether and water, and the inorganic layer was extracted with ether. The combined organic phases were dried over and the crude materil was purified by column chromatography with ETOAc/hexane to give 5.86 g (83%)5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid.

後処理

  1. additionthe slurry was diluted
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ether
  4. extractionwater, and the inorganic layer was extracted with ether
  5. customThe combined organic phases were dried over and the crude materil
  6. customwas purified by column chromatography with ETOAc/hexane

出典と根拠

ORDレコード
ord-6ed6edff7c4840dc8c5284f235649c74
出典データセット
uspto-grants-2005_02
特許番号
US06858651B2

関連ノート

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