A convenient synthesis of amino acid methyl esters

Molecules

Volumn 13, Issue 5, 2008, Pages 1111-1119

  Li, Jiabo ^a   Sha, Yaowu ^a  

^a Tsinghua University   (China)

Author keywords

Amino acid methyl ester hydrochlorides; Amino acids; Esterification; Trimethylchlorosilane

Indexed keywords

AMINO ACID; CHLOROTRIMETHYLSILANE; ESTER; METHANOL; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMISTRY; ESTERIFICATION; SYNTHESIS;

AMINO ACIDS; ESTERIFICATION; ESTERS; METHANOL; TRIMETHYLSILYL COMPOUNDS;

EID: 44449160328     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13051111     Document Type: Article

References (38)

1. Barrett, G.C. 'Amino Acids, Peptides and Proteins' R.S.C. Publications: London 1996, 27, 1
2. Manjinder, S.L.; Yeeman, K.R.; Michael, N.G. J.; John, C.V. Serine and Threonine β-Lactones: A New Class of Hepatitis A Virus 3C Cysteine Proteinase Inhibitors. J. Org. Chem. 2002, 67, 1536-1547.
3. Tandon, V.K.; Yadav, D.B.; Singh, R.V.; Chaturvedi, A.K.; Shukla, P.K. Synthesis and activity of oleanolic acid derivatives, a novel class of inhibitors of osteoclast formation. Bioorg. Med. Chem. Lett. 2005, 15, 5324-5328.
4. Tomasz, Z.; Michał, A.; Janusz, J. A simple synthesis of chiral macrocyclic tetraamides derived from α-amino acids. Tetrahedron: Asymmetry 2002, 13, 2053-2059.
5. Kim, J.; Kim, J.; Song, S.; Jung, O.; Suh, H. Enantiomeric Recognition of D- and L-Amino Acid Methyl Ester Hydrochlorides by New Chiral Bis -pyridino-18-crown-6 Substituted with Urea, and Diphenyl Groups. J. Incl. Phenom. Macrocycl. Chem. 2007, 58, 187-192.
6. Somlai, C.; Peter, A.; Forgo, P.; Penke, B. One-Pot Synthesis of N-Protected β-Chiral Amino Alcohols. Synth. Commun. 2003, 33, 1815-1820.
7. Pollini, G.; Baricordi, N.; Benetti, S.; De Risi, C.; Zanirato, V. A simple entry to chiral nonracemic 2-piperazinone derivatives. Tetrahedron Lett. 2005, 46, 3699-3701.
8. Atsushi, N.; Toyoharu, M.; Hiroto, K.; Takeshi, E. Controlled Cationic Ring-Opening Polymerization of 1,3-Oxazolidine-2-thione Derived from L-Serine. Macromolecules 2003, 36, 9335-9339.
9. Fumio, S.; Takeshi, E. Syntheses and functions of polymers based on amino acids. Macromol. Chem. Phys. 1999, 200, 2651-2661.
10. Pher, G.A.; David, G.; David, T. Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines. J. Org. Chem. 1997, 62, 7364-7375.
11. Simon, M.J.; Jonathan, E.U.; Marcel, K.; Reto, B.; John, L.H.; Colin, B.; Ian, H. G. Analogues of Thiolactomycin as Potential Antimalarial Agents. J. Med. Chem. 2005, 48, 5932-5941.
12. Julian, R.R. The Methyl Esterification of Amino Acids with 2,2-Dimethoxypropane and Aqueous Hydrogen. J. Org. Chem. 1963, 28, 2898.
13. Ramesh, C.A.; Vimal. A mild and convenient procedure for the esterification of amino acids. Synth. Commun. 1998, 28, 1963-1965.
14. Nakao, R.; Oka, K.; Fukumoto, T. A Simple Method for the Esterification of Carboxylic acids Using Chlorosilanes. Bull. Chem. Soc. Japan. 1981, 54, 1267-1268.
15. Brook, M.A.; Chan, T.H. A Simple Procedure for the Esterification of Carboxylic Acids. Synthesis, 1983, 201-203
16. Chen, B.C.; Amanda, P.S.; Guo, P.; Mark, S.B.; Octavian, R.K.; Joseph, E.S.; Gregory, D.V. A Facile Method for the Transformation of N-(tert-Butoxycarbonyl) α-Amino Acids to N-Unprotected α-Amino Methyl Esters. J. Org. Chem. 1999, 64, 9294-9296.
17. Omar, M.; Eusebio, J. Enantioselective alkylation and protonation of prochiral enolates in the asymmetric synthesis of β-amino acids. Tetrahedron, 2003, 59, 4223-4229.
18. Debrabandere, V. I.; Stockl, D.; Thienpont, L. M.; De Leenheer, A. P. J. Mass. Spectrom. 1998, 33, 1032.
19. Lebedev, A.V.; Lebedeva, A.B.; Sheludyakov, V.D.; Shatunov, V.V.; Ovcharuk, S.N. Organosilicon Synthesis of Isocyanates: IV. Synthesis of Isocyanates from Aliphatic and Alkylaromatic Amino Acid Esters. Russ. J. Gen. Chem. 2007, 77, 581-585.
20. Corey, E.J.; Ishihara, K. Highly enantioselective catalytic Diels-Alder addition promoted by a chiral bis(oxazoline)-magnesium complex. Tetrahedron Lett. 1992, 33, 6807-6810.
21. Gros, L.; Lorente, S. O.; Jimenez, C. J.; Yardley, V.; Rattray, L.; Wharton, H.; Little, S.; Croft, S. L.; Ruiz-Perez, L. M.; Gonzalez-Pacanowska, D.; Gilbert, I. H. Evaluation of Azasterols as Anti-Parasitics. J. Med. Chem. 2006, 49, 6094-6103.
22. Mancilla, T.; Carrillo, L.; Zamudio-Rivera, L.S.; Beltran, H.I.; Farfan, N. Synthesis and characterization of piperazine-2,6-diones. Org. Prep. Proced. Int. 2002, 34, 87-94
23. White, B.D.; Mallen, J.; Arnold, K.A.; Fronczek, F.R.; Gandour, R.D.; Gehrig, L.M.B.; Gokel, G. W. Peptide side-arm derivatives of lariat ethers and bibracchial lariat ethers: syntheses, cation binding properties, and solid state structural data. J. Org. Chem. 1989, 54, 937-947.
24. Garmaise, D.L.; Schwartz, R.; McKay, A. F. Amino acids. VI. Preparation and chemistry of ω-carbalkoxyalkyl isothiocyanates. J. Am. Chem. Soc. 1958, 80, 3332-3334.
25. Carmi, C.; Cavazzoni, A.; Zuliani, V.; Lodola, A.; Bordi, F.; Plazzi, P.V.; Alfieri, R.R.; Petronini, P.G.; Mor, M. 5-Benzylidene-hydantoins as new EGFR inhibitors with antiproliferative activity. Bioorg. Med. Chem. Lett. 2006, 16, 4021-4025.
26. Ian, W.J.S, Juris, R.S. Synthesis of N(10)-acetyleudistomin L. Tetrahedron Lett. 1989, 30, 1041-1044.
27. Ziakas, G.N.; Rekka, E.A.; Gavalas, A.M.; Eleftheriou, P.T.; Kourounakis, P.N. New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents. Bioorg. Med. Chem. 2006, 14, 5616-5624.
28. Song, Q.H.; Tang, W.J.; Hei, X.M.; Wang, H.B; Guo, Q.X; Yu, S.Q. Efficient photosensitized splitting of thymine dimer by a covalently linked tryptophan in solvents of high polarity. Eur. J. Org. Chem. 2005, 6, 1097-1106.
29. Driffield, M.; Goodall, D.M.; Smith, D.K. Syntheses of dendritic branches based on L-lysine: is the stereochemistry preserved throughout the synthesis? Org. Biomol. Chem. 2003, 1, 2612-2620.
30. Wang, G.J.; Lai, T.C.; Chen, C. Inhibitory effects of L-arginine derivatives on endotheliumdependent vasorelaxing response to acetylcholine of the rat aorta. Eur. J. Med. Chem. 2004, 39, 611-617.
31. Cox, R.J.; Gibson, J.S.; Martin, M.B.M. Aspartyl phosphonates and phosphoramidates: the first synthetic inhibitors of bacterial aspartate-semialdehyde dehydrogenase. ChemBioChem. 2002, 3, 874-886.
32. Sellarajah, S.; Lekishvili, T.; Bowring, C.; Thompsett, A.R.; Rudyk, H.; Birkett, C.R.; Brown, D.R.; Gilbert, I.H. Synthesis of Analogues of Congo Red and Evaluation of Their Anti-Prion Activity. J. Med. Chem. 2004, 47, 5515-5534.
33. Elhadi, F.E.; Ollis, W.D.; Stoddart, J.F. Conformational behavior of medium-sized rings. Part15. 1,19,17-Triaza[2.2.2]metacyclophane-2,10,18-trione derivatives. J. Chem. Soc., Perkin 1 1982, 8, 1727-32.
34. Howard, N.I.; Bugg, T.D.H. Synthesis and activity of 5′-Uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A. Bioorg. Med. Chem. 2003, 11, 3083-3099.
35. 2O (L=DTPA-bis(4-carboxylicphenyl) amide). Bull. Kor. Chem. Soc. 2006, 27, 1038-1042.
36. Samanta, S. Novel orally administrable antidiabetic of small chain cyclic peptides, their synthesis and therapeutic compositions. Indian Pat. Appl. 2005KO00090, 2006.
37. Ten C.A.T.; Dankers, P.Y.W.; Kooijman, H.; Spek, A.L.; Sijbesma, R.P.; Meijer, E.W. Enantioselective Cyclization of Racemic Supramolecular Polymers. J. Am. Chem. Soc. 2003, 125, 6860-6861.
38. Reymond, J.L.; Chen, Y. Catalytic, Enantioselective Aldol Reaction with an Artificial Aldolase Assembled from a Primary Amine and an Antibody. J. Org. Chem. 1995, 60, 6970-6979.