Triethylamine → (2S)-N-[(1S)-1-Formyl-3-methylbutyl]-3-methyl-2-[(2-naphthalenylsulfonyl)amino]butanamide

HRID 323547Notes

Reaction equation

HRID 323547 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([CH2:27][OH:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH:16]([CH3:18])[CH3:17])(=[O:13])=[O:12].C(N(CC)CC)C.C(OCC)(=O)C>CS(C)=O.ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([CH:27]=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH:16]([CH3:18])[CH3:17])(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10916536HCID 10916536, compound

Product 1

HCID 10883981(2S)-N-[(1S)-1-Formyl-3-methylbutyl]-3-methyl-2-[(2-naphthalenylsulfonyl)amino]butanamideYield 75.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N-(2-Naphthalenesulfonyl)-L-valyl-L-leucinol (1.3 g) was dissolved in dimethyl sulfoxide (20 ml) and dichloromethane (10 ml), and triethylamine (1.9 g) was added. The solution was stirred at room temperature while adding a solution (20 ml) of sulfur trioxide-pyridine complex (2.0 g) in dimethyl sulfoxide, which was followed by stirring for 2 hr. After the completion of the reaction, ethyl acetate was added. The mixture was washed with dilute hydrochloric acid, saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with a mixed solution of hexane-ethyl acetate to give 0.98 g of N-(2-naphthalenesulfonyl)-L-valyl-L-leucinal (Compound 34) as white crystals. [Step 1]

Workup

  1. stirringby stirring for 2 hr
  2. additionwas added
  3. washThe mixture was washed with dilute hydrochloric acid, saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with a mixed solution of hexane-ethyl acetate

Sources & evidence

ORD record
ord-263c245ed249450285d6c89f93b56c27
Source dataset
uspto-grants-2001_04
Patent number
US06214800B1

Reaction notes

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