N-Methylpiperidine → [(R)-1-(6-Fluoro-2-benzothiazolyl)ethyl]-N2-isopropoxycarbonyl-L-valinamide

HRID 481466ノート

反応式

HRID 481466 の反応式
C[N:2]1CCCCC1.[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.[F:30][C:31]1[CH:42]=[CH:41][C:34]2[N:35]=[C:36]([C@H:38](N)[CH3:39])[S:37][C:33]=2[CH:32]=1>C(Cl)Cl>[F:30][C:31]1[CH:42]=[CH:41][C:34]2[N:35]=[C:36]([C@H:38]([N:14]([C:12]([O:11][CH:8]([CH3:9])[CH3:10])=[O:13])[C@H:15]([C:19]([NH2:2])=[O:21])[CH:16]([CH3:17])[CH3:18])[CH3:39])[S:37][C:33]=2[CH:32]=1

参加物

6

反応物 4

HCID 12291N-MethylpiperidineHCID 62365Isobutyl chloroformateHCID 10921462(R)-1-(6-Fluorobenzo[D]thiazol-2-YL)ethanamineHCID 11063514(2S)-3-methyl-2-(((propan-2-yloxy)carbonyl)amino)butanoic acid

生成物 1

HCID 69502376[(R)-1-(6-Fluoro-2-benzothiazolyl)ethyl]-N2-isopropoxycarbonyl-L-valinamide収率 63.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

0.4 g of N-methylpiperidine was added to a solution containing 0.8 g of N-isopropoxycarbonyl-L-valine dissolved in 25 ml of methylene chloride, at -20° C. After the mixture was stirred for 10 minutes at the same temperature, 0.6 g of isobutyl chloroformate was added to the mixture at -20° C., and stirred for 1 hour at -20° C.~-10° C. After 0.8 g of (R)-1-(6-fluoro-2-benzothiazolyl)ethylamine was added to this mixture at -60° C., the refrigerant was put off, and then the reaction mixture was warmed naturally to room temperature while being stirred. After completion of the reaction, the resulting 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 then the solvent was removed under reduced pressure. The obtained crude crystals were purified by column chromatography on silica gel, thus yielding 0.95 g of the desired product in the form of a white powder (yield: 63%).

後処理

  1. additionwas added to the mixture at -20° C.
  2. stirringwhile being stirred
  3. customAfter completion of the reaction
  4. washthe resulting 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. customThe obtained crude crystals
  8. customwere purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-8dbf6dae56c749f599cb392458128597
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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