L-Leucine → Acetophenone

HRID 277657Notes

Reaction equation

HRID 277657 reaction equation
[OH-].[Na+].N[C@H:4](C(O)=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N[C@H](C(O)=[O:22])CC(C)C.N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1.N[C@H](C(O)=O)[C@H](CC)C.COC1C=CC(C[C@@H](C(O)=O)N)=CC=1>O1CCOCC1.O>[C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:22])[CH3:4]

Participants

9

Reactant 6

HCID 6106L-LeucineHCID 6140L-PhenylalanineHCID 6305L-TryptophanHCID 6306L-IsoleucineHCID 14798Sodium HydroxideHCID 2723935O-Methyl-L-Tyrosine

Product 1

HCID 7410Acetophenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

200 μl (50 μmol) of a 0.25 M solution of each of the isatins listed in Table 1, in dioxane; 200 μl (50 μmol) of a 0.25 M solution of the α-amino acids listed in Table 2, in water (including 1 equivalent of sodium hydroxide for the L-phenylalanine, L-leucine, O-benzyl-(D,L)-serine, L-tryptophan, L-isoleucine, and O-methyl-L-tyrosine); and 400 μl (50 μmol) of a 0.125 M solution containing the chalcones produced by reaction of the arylaldehydes and acetophenone compounds of Tables 3 and 4, in dioxane, were combined in 1 ml perfume vials. The vials were capped and heated at 80° C. overnight. The solvent was then evaporated under reduced pressure and the resulting products were all recovered in greater than 85% purity according to high pressure liquid chromatography (HPLC) and mass spectroscopy (MS) experiments.

Sources & evidence

ORD record
ord-ee6776db180d46219c8cd1b78d0330a2
Source dataset
uspto-grants-2002_03
Patent number
US06358750B1

Reaction notes

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