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

HRID 481467Notes

Reaction equation

HRID 481467 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-11e180d4e96745e29aaf576ab8848b60
Source dataset
uspto-grants-1998_08
Patent number
US05789428

Reaction notes

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