Novel Glycine Derivative Capable Of Inhibiting Melanin Formation And Composition Using The Same
a technology of glycine derivative and melanin, which is applied in the field of glycine derivative, can solve the problems of skin allergy, kojic acid stability, and inability to completely realize the mechanism of inhibiting melanin formation of various effective skin whitening ingredients, and achieve the effect of increasing the stability of the formulation and not easily oxidizing
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example 1
preparation of 3(2-acetylamino-acetylamino)-propionic acid or Acetyl-Glycine-β-Alanine
[0035]Ac-Gly-OH a (3.77 g, 32.2 mmol) and triethylamine (6.7 mL, 48.1 mmol) were dissolved in 160 mL THF and cooled to −10□, and isobutylchloroformate (5.02 g, 38.6 mmol) was added. The mixture was stirred at −10□ for 1 hr. H-beta-Ala-OBzl.PTSA e (11.26 g, 32.0 mmol) and triethylamine (6.7 mL, 48.1 mmol) was dissolved in 160 mL THF, and added into mix anhydride solution. The reaction mixture was stirred at room temperature overnight. The salt was filtrated off and THF was removed in vacuum. The residue obtained was purified by column chromatography using ethyl acetate and heptane as eluent to obtain 5.95 g Ac-Gly-beta-Ala-OBzl f.
[0036]Ac-Gly-beta-Ala-OBzl f was dissolved in 200 mL THF, and then added 10% Pd / C. The mixture was stirred under hydrogen. After overnight, the catalyst was removed by filtration and the resulting filtrate was evaporated to 2.49 g white powder g. (yield=41.0%, purity>95%). ...
example 2
preparation of 4-(2-Acetylamino-acetylamino)-butyric acid or Acetyl-Glycine-γ-aminobutyric acid
[0037]Ac-Gly-OH a (2.52 g, 21.6 mmole) and triethylamine (5 ml, 36.1 mmole) were dissolved in THF (100 ml) and cooled to −10° C., and isobutylchloroformate (3.2 g, 23.8 mmole) was added. The mixture was stirred at −10° C. for 1 hr. H-γ Abu-OBzl.PTSA h (7.6 g, 20.8 mmole) and triethylamine (5 ml, 36.1 mmole) was dissolved in THF (90 ml), and added into mix anhydride solution at −5° C. The reaction mixture was stirred at room temperature overnight. The salt was filtrated off and THF was removed in vacuum. The residue was purified by column chromatography using ethyl acetate and heptane as eluent to obtain Ac-Gly-GABA-OBzl i.
[0038]The column purified Ac-Gly-γ Abu-OBzl i (2.6 g) was dissolved in THF (100 ml), and then added 5% Pd / C (0.26 g). The mixture was stirred under hydrogen. After overnight, the catalyst was removed by filtration and the resulting filtrate was evaporated to white powder ...
example 3
preparation of [(2-Acetylamino-acetyl)-methyl-amino]acetic acid) or Acetyl-Glycine-Sarcosine
[0039]Ac-Gly-OH a (4.10 g, 35.0 mmol), Sar-OBzl.PTSA b (11.71 g, 33.3 mmol), triethylamine (5.58 mL, 40.0 mmol), HOBt (1.35 g, 10 mmol) and DCC (8.25 g, 40.0 mmol) were stirred in 200 mL THF overnight. The mixture was filtered to discard DCU and removed THF in vacuum. The concentrated residue was dissolved in 100 mL ethyl acetate and washed with 100 mL 10% citric acid(aq) twice, 100 mL 5% NaHCO3(aq) twice and 100 mL brine twice, dried over MgSO4, and evaporated in vacuum to get about 9 g light yellow oily Ac-Gly-Sar-OBzl c.
[0040]Ac-Gly-Sar-OBzl was dissolved in 200 mL THF, and then added 10% Pd / C. The mixture was stirred under hydrogen. After overnight, methanol was added to dissolve product. The catalyst was removed by filtration and removed solvent in vacuum. The concentrate residue was recrystallized from THF to obtain 4.49 g white powder d (yield=71.6%, purity>95%). The compound was chara...
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