Sodium Bicarbonate → 2,2-diphenyl-5-[N-(4-methanesulphonamidophenethyl)-N-methylamino]pentanamide

HRID 1463862ノート

反応式

HRID 1463862 の反応式
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][NH:14][CH3:15])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[CH:31][CH:30]=1)(=O)=O.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:11][CH2:12][CH2:13][N:14]([CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([NH:35][S:36]([CH3:39])(=[O:37])=[O:38])=[CH:33][CH:34]=2)[CH3:15])[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 149859624-Methanesulphonamidophenethyl mesylateHCID 190884752,2-Diphenyl-5-methylaminopentanamide

生成物 1

HCID 190884862,2-diphenyl-5-[N-(4-methanesulphonamidophenethyl)-N-methylamino]pentanamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 2,2-diphenyl-5-methylaminopentanamide (0.3 g--see Preparation 3), N-[4-(2-methanesulphonyloxyethyl)phenyl]-methanesulphonamide (0.3 g--see Preparation 18), sodium bicarbonate (0.5 g) and acetonitrile (10 ml) was heated under reflux for 8 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated and the aqueous layer extracted with dichloromethane (2×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a foam, yield 0.12 g.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. customThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×20 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with dichloromethane
  10. additioncontaining methanol (0% up to 6%)
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3dbedb350bc0453ea42b54a5264fdcbc
出典データセット
uspto-grants-1994_04
特許番号
US05302595

反応ノート

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