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

HRID 1106406Notes

Reaction equation

HRID 1106406 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.

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-fda1f8efeb6548b09e6af7dd3d9a0792
Source dataset
uspto-grants-2000_05
Patent number
US06057290

Reaction notes

Loading…