(S)-2-HexanaMido-3-(4-hydroxyphenyl)propanoic acid synthesis
- Product Name:(S)-2-HexanaMido-3-(4-hydroxyphenyl)propanoic acid
- CAS Number:86432-28-2
- Molecular formula:C15H21NO4
- Molecular Weight:279.33
1104874-94-3
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86432-28-2
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Yield:86432-28-2 98%
Reaction Conditions:
Stage #1: (S)-methyl 2-(hexanamido)-3-(4-hydroxyphenyl)propanoatewith lithium hydroxide in tetrahydrofuran;water at 20; for 16 h;
Stage #2: with hydrogenchloride in water;
Steps:
2.4 General procedure for synthesis of N-fatty acyl-L-tyrosine
General procedure: N-fatty acyl-L-tyrosine methyl esters (2-6) (1 eq.) were dissolved in THF: H2O (7:3) and LiOH added (3 eq.), stirred the reaction mixture at RT for 16 h. After completion of the reaction, the mixture was concentrated under vacuum to obtain a white precipitate. This white precipitate was neutralized with 2 N HCl and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated to yield a white solid. This solid with little impurity was purified by silica gel chromatography using a gradient of chloroform/methanol (95:5, v/v) to obtain a yield (96 - 98%) of the title compound as a solid.
References:
Vudhgiri, Srikanth;Prasad;Poornachandra;Ganesh Kumar;Anjaneyulu;Sirisha;Jala, Ram Chandra Reddy [Journal of Chemical Sciences,2017,vol. 129,# 6,p. 663 - 677]
1080-06-4
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86432-28-2
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60-18-4
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86432-28-2
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