N-Methylpiperidine → N-(t-butoxycarbonyl)-L-valine 4-methoxy-1-phenylethylamide

HRID 248323

反応式

HRID 248323 の反応式
CN1CCCCC1.[C:8]([O:12][C:13]([NH:15][C@H:16]([C:20]([OH:22])=O)[CH:17]([CH3:19])[CH3:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].ClC(OCC(C)C)=O.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]([NH2:41])[CH3:40])=[CH:35][CH:34]=1>C(Cl)Cl>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]([NH:41][C:20](=[O:22])[C@H:16]([CH:17]([CH3:18])[CH3:19])[NH:15][C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])[CH3:40])=[CH:35][CH:34]=1

参加物

6

反応物 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 83693Boc-L-ValineHCID 2381811-(4-Methoxyphenyl)ethanamine

生成物 1

HCID 14774435N-(t-butoxycarbonyl)-L-valine 4-methoxy-1-phenylethylamide収率 217.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-60 °C

実験手順

2.3 g (0.023 mol) of N-methylpiperidine are added to 5.0 g of t-butoxycarbonyl-L-valine (0.023 mol), dissolved in 50 ml of CH2Cl2, at -20° C. 3.2 g (0.023 mol) of isobutyl chloroformate are then rapidly added dropwise at -20° C., the mixture is subsequently stirred at the same temperature for 10 minutes and cooled to -60° C. and 3.5 g (0.023 mol) of 4-methoxy-1-phenylethylamine are allowed to run in, the temperature being kept below -15° C. After 2 hours at -15° C., the mixture is subsequently stirred at room temperature for 15 hours, the solid is filtered off and rinsed with CH2Cl2, the filtrate is concentrated, the residue is introduced into water, the mixture is extracted twice with ethyl acetate and the combined ethyl acetate phases are washed with NaHCO3 solution and water, dried and concentrated. 17.5 g (85% of theory) of N-(t-butoxycarbonyl)-L-valine 4-methoxy-1-phenylethylamide of melting point 126°-127° C. are obtained.

後処理

  1. custombeing kept below -15° C
  2. waitAfter 2 hours at -15° C.
  3. stirringthe mixture is subsequently stirred at room temperature for 15 hours
  4. filtrationthe solid is filtered off
  5. washrinsed with CH2Cl2
  6. concentrationthe filtrate is concentrated
  7. additionthe residue is introduced into water
  8. extractionthe mixture is extracted twice with ethyl acetate
  9. washthe combined ethyl acetate phases are washed with NaHCO3 solution and water
  10. customdried
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-82146073056f4aa1ba339f9fa262aa86
出典データセット
uspto-grants-1993_05
特許番号
US05210084

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