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

HRID 1587854노트

반응식

HRID 1587854 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dc596697d5664a0aae3c9f418c52209e
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05219871

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