N-Methylpiperidine → N1-[1-(2-Benzothiazolyl)ethyl]-N2-isopropoxycarbonyl-L-valinamide

HRID 481467ノート

反応式

HRID 481467 の反応式
CN1CCCCC1.[CH:8]([O:11][C:12]([NH:14][C@H:15]([C:19]([OH:21])=O)[CH:16]([CH3:18])[CH3:17])=[O:13])([CH3:10])[CH3:9].ClC(OCC(C)C)=O.[S:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[CH:39]([NH2:41])[CH3:40]>C(Cl)Cl>[S:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[C:31]1[CH:39]([NH:41][C:19](=[O:21])[C@H:15]([CH:16]([CH3:17])[CH3:18])[NH:14][C:12]([O:11][CH:8]([CH3:9])[CH3:10])=[O:13])[CH3:40]

参加物

6

反応物 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 11063514(2S)-3-methyl-2-(((propan-2-yloxy)carbonyl)amino)butanoic acidHCID 112061111-(1,3-Benzothiazol-2-yl)ethan-1-amine

生成物 1

HCID 70266697N1-[1-(2-Benzothiazolyl)ethyl]-N2-isopropoxycarbonyl-L-valinamide収率 58.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

0.3 g of N-methylpiperidine was added to a solution containing 0.6 g of N-isopropoxycarbonyl-L-valine dissolved in 40 mL of methylene chloride, at -20° C., and then the mixture was stirred for 10 minutes at the same temperature. 0.4 g of isobutyl chloroformate was added to the mixture at -40° C., and then stirred for 1 hour at -40° C. to -15° C. After 0.5 g of 1-(2-benzothiazolyl)ethylamine was added to this mixture at -60° C. and the refrigerant was put off, the reaction mixture was warmed naturally to room temperature while being stirred. After completion of the reaction, the reaction mixture was washed successively with water, a 5% aqueous solution of sodium bicarbonate, and water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue, which was a crude crystal, was purified by column chromatography on silica gel, thus yielding 0.6 g of the desired product in the form of a white powder (yield: 59%).

後処理

  1. stirringstirred for 1 hour at -40° C. to -15° C
  2. stirringwhile being stirred
  3. customAfter completion of the reaction
  4. washthe reaction mixture was washed successively with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customwas purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-11e180d4e96745e29aaf576ab8848b60
出典データセット
uspto-grants-1998_08
特許番号
US05789428

反応ノート

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