Triethylamine → HCID 11122265, compound

HRID 1266968Notes

Reaction equation

HRID 1266968 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([C:16]([NH:18][C@@H:19]([CH2:24][OH:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(OCC)(=O)C>CS(C)=O.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@@H:12]([C:16]([NH:18][C@@H:19]([CH:24]=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10970796HCID 10970796, compound

Product 1

HCID 11122265HCID 11122265, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

N-(4-Fluorophenylsulfonyl)-D-valyl-D-leucinol (1.5 g) was dissolved in dimethyl sulfoxide (20 ml) and dichloromethane (10 ml), and triethylamine (2.4 g) was added. The solution was stirred at room temperature while adding a solution (20 ml) of sulfur trioxide-pyridine complex (2.6 g) in dimethyl sulfoxide, which was followed by stirring for 1 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 purified by preparative TLC plate (developing solvent: hexane-ethyl acetate, 1:1, v/v) to give 1.0 g of N-(4-fluorophenylsulfonyl)-D-valyl-D-leucinal (Compound 55) as white crystals. [Step 1]

Workup

  1. stirringby stirring for 1 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. customthe residue was purified by preparative TLC plate (

Sources & evidence

ORD record
ord-33e7aa2018e24e7e9727395c5524e6fb
Source dataset
uspto-grants-2003_04
Patent number
US06551999B1

Reaction notes

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