메뉴 건너뛰기




Volumn 9, Issue 1, 2008, Pages 33-44

Microwave-assisted esterification of N-acetyl-L-phenylalanine using modified Mukaiyama's reagents: A new approach involving ionic liquids

Author keywords

Amino acid; Esterification; Ionic liquid; Microwave; Mukaiyama's reagent

Indexed keywords

2 CHLORO 2 METHYLPYRIDINIUM IODIDE; DICHLOROMETHANE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; N ACETYLPHENYLALANINE; PHENYLALANINE DERIVATIVE; PYRIDINIUM DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

EID: 39349113316     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms9010033     Document Type: Article
Times cited : (20)

References (46)
  • 4
    • 0002738319 scopus 로고
    • Esterification of carboxylic acid with ethanol accompanied by pervaporation
    • Kita, H.; Sasaki, S.; Tanaka, K.; Okamoto, K.; Yamamoto, M. Esterification of carboxylic acid with ethanol accompanied by pervaporation. Chem. Lett. 1988, 2025-2028.
    • (1988) Chem. Lett , pp. 2025-2028
    • Kita, H.1    Sasaki, S.2    Tanaka, K.3    Okamoto, K.4    Yamamoto, M.5
  • 5
    • 33845550436 scopus 로고
    • A simple and convenient method for esterification of tryptophan and other amino acids
    • Arai, I.; Muramatsu, I. A simple and convenient method for esterification of tryptophan and other amino acids. J. Org. Chem. 1983, 48, 121-123.
    • (1983) J. Org. Chem , vol.48 , pp. 121-123
    • Arai, I.1    Muramatsu, I.2
  • 6
    • 33947448737 scopus 로고
    • Benzyl esters of amino acids
    • Miller, H. K.; Waelsch, H. Benzyl esters of amino acids. J. Am. Chem. Soc. 1952, 74, 1092-1093.
    • (1952) J. Am. Chem. Soc , vol.74 , pp. 1092-1093
    • Miller, H.K.1    Waelsch, H.2
  • 9
    • 33947474297 scopus 로고
    • A further comparison of the behavior of analogous aromatic and hydroaromatic substrates of α-chymotrypsin
    • Jones, J. B.; Niemann, C. A further comparison of the behavior of analogous aromatic and hydroaromatic substrates of α-chymotrypsin. Biochemistry 1963, 2, 498-500.
    • (1963) Biochemistry , vol.2 , pp. 498-500
    • Jones, J.B.1    Niemann, C.2
  • 11
    • 0002694516 scopus 로고
    • Cesium fluoride-promoted synthesis of carboxylic acid derivatives using 2-fluoropyridinium salt
    • Shoda, S.; Mukaiyama, T. Cesium fluoride-promoted synthesis of carboxylic acid derivatives using 2-fluoropyridinium salt. Chem. Lett. 1980, 391-392.
    • (1980) Chem. Lett , pp. 391-392
    • Shoda, S.1    Mukaiyama, T.2
  • 12
    • 0000688610 scopus 로고
    • Cesium fluoride-promoted esterification of carboxylic acids. A practical alternative to the diazomethane method and direct conversion of organotin carboxylates
    • Sato, T.; Otera, J.; Nozaki, H. Cesium fluoride-promoted esterification of carboxylic acids. A practical alternative to the diazomethane method and direct conversion of organotin carboxylates. J. Org. Chem. 1992, 57, 2166-2169.
    • (1992) J. Org. Chem , vol.57 , pp. 2166-2169
    • Sato, T.1    Otera, J.2    Nozaki, H.3
  • 13
    • 33746133531 scopus 로고    scopus 로고
    • An effective chemoselective esterification of hydroxybenzoic acids in ionic liquid promoted by KF
    • Biondini, D.; Brinchi, L.; Germani, R.; Savelli, G. An effective chemoselective esterification of hydroxybenzoic acids in ionic liquid promoted by KF. Lett. Org. Chem. 2006, 3, 207-211.
    • (2006) Lett. Org. Chem , vol.3 , pp. 207-211
    • Biondini, D.1    Brinchi, L.2    Germani, R.3    Savelli, G.4
  • 14
    • 3242766028 scopus 로고    scopus 로고
    • A new method for the esterification of carboxylic acids with various alcohols by using di-2-thienyl carbonate, a new coupling reagent
    • Mukaiyama, T.; Oohashi, Y.; Fukumo, K. A new method for the esterification of carboxylic acids with various alcohols by using di-2-thienyl carbonate, a new coupling reagent. Chem. Lett. 2004, 33, 552-553.
    • (2004) Chem. Lett , vol.33 , pp. 552-553
    • Mukaiyama, T.1    Oohashi, Y.2    Fukumo, K.3
  • 15
    • 0007511516 scopus 로고
    • New synthetic reactions based on the onium salts of aza-arenes
    • Mukaiyama, T. New synthetic reactions based on the onium salts of aza-arenes. Angew. Chem. Int. Ed. Engl. 1979, 18, 707-721.
    • (1979) Angew. Chem. Int. Ed. Engl , vol.18 , pp. 707-721
    • Mukaiyama, T.1
  • 16
    • 0001300818 scopus 로고
    • A convenient method for the synthesis of carboxylic esters
    • Mukaiyama, T.; Usui, M.; Shimada, E.; Saigo, K. A convenient method for the synthesis of carboxylic esters. Chem. Lett. 1975, 1045-1048.
    • (1975) Chem. Lett , pp. 1045-1048
    • Mukaiyama, T.1    Usui, M.2    Shimada, E.3    Saigo, K.4
  • 18
    • 10044264447 scopus 로고    scopus 로고
    • Polymer-supported mukaiyama reagent: A useful coupling reagent for the synthesis of esters and amides
    • Crosignani, S.; Gonzalez, J.; Swinnen, D. Polymer-supported mukaiyama reagent: A useful coupling reagent for the synthesis of esters and amides. Org. Lett. 2004, 6, 4579 -4582.
    • (2004) Org. Lett , vol.6 , pp. 4579-4582
    • Crosignani, S.1    Gonzalez, J.2    Swinnen, D.3
  • 19
    • 15944366537 scopus 로고    scopus 로고
    • A rapid microwave-assisted esterification utilizing the Mukaiyama supported reagent
    • Donati, D.; Morelli, C.; Taddei, M. A rapid microwave-assisted esterification utilizing the Mukaiyama supported reagent. Tetrahedron Lett. 2005, 46, 2817-2819.
    • (2005) Tetrahedron Lett , vol.46 , pp. 2817-2819
    • Donati, D.1    Morelli, C.2    Taddei, M.3
  • 20
    • 1842788698 scopus 로고    scopus 로고
    • Preparation and evaluation of a polymer-supported Mukaiyama reagent
    • Convers, E.; Tye, H.; Whittaker, M. Preparation and evaluation of a polymer-supported Mukaiyama reagent. Tetrahedron Lett. 2004, 45, 3401-3404.
    • (2004) Tetrahedron Lett , vol.45 , pp. 3401-3404
    • Convers, E.1    Tye, H.2    Whittaker, M.3
  • 21
    • 10844283659 scopus 로고    scopus 로고
    • A new polymer-supported reagent for the synthesis of β-lactams in solution
    • Donati, D.; Morelli, C.; Porcheddu, A.; Taddei, M. A new polymer-supported reagent for the synthesis of β-lactams in solution. J. Org. Chem. 2004, 69, 9316-9318.
    • (2004) J. Org. Chem , vol.69 , pp. 9316-9318
    • Donati, D.1    Morelli, C.2    Porcheddu, A.3    Taddei, M.4
  • 22
    • 0035923960 scopus 로고    scopus 로고
    • New developments in catalysis using ionic liquids
    • Gordon, C. M. New developments in catalysis using ionic liquids. Appl. Cat. A: General. 2001, 222, 101-117.
    • (2001) Appl. Cat. A: General , vol.222 , pp. 101-117
    • Gordon, C.M.1
  • 23
    • 22944447442 scopus 로고    scopus 로고
    • Ionic liquids: The route to cleaner and more efficient fine chemical synthesis?
    • Feb 25
    • Houlton, S. Ionic liquids: the route to cleaner and more efficient fine chemical synthesis? Chem. Week. 2004, Feb 25, s10-s11.
    • (2004) Chem. Week
    • Houlton, S.1
  • 24
    • 0031127122 scopus 로고    scopus 로고
    • Ionic liquids for clean technology
    • Seddon, K. R. Ionic liquids for clean technology. J. Chem. Technol. Biotechnol. 1997, 68, 351-356.
    • (1997) J. Chem. Technol. Biotechnol , vol.68 , pp. 351-356
    • Seddon, K.R.1
  • 25
    • 0347417134 scopus 로고    scopus 로고
    • Room-temperature ionic liquids - solvents for synthesis and catalysis
    • Welton, T. Room-temperature ionic liquids - solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071-2083.
    • (1999) Chem. Rev , vol.99 , pp. 2071-2083
    • Welton, T.1
  • 26
    • 0036998098 scopus 로고    scopus 로고
    • Applications of ionic liquids in organic synthesis
    • Zhao, H.; Malhotra, S. V. Applications of ionic liquids in organic synthesis. Aldrichimica Acta. 2002, 35, 75-83.
    • (2002) Aldrichimica Acta , vol.35 , pp. 75-83
    • Zhao, H.1    Malhotra, S.V.2
  • 28
    • 12344296667 scopus 로고    scopus 로고
    • Chemical and biochemical transformations in ionic liquids
    • Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Chemical and biochemical transformations in ionic liquids. Tetrahedron. 2005, 61, 1015-1060.
    • (2005) Tetrahedron , vol.61 , pp. 1015-1060
    • Jain, N.1    Kumar, A.2    Chauhan, S.3    Chauhan, S.M.S.4
  • 29
    • 0004573120 scopus 로고
    • Exchange reactions of α-halogenated pyridines
    • Bradlow, H. L.; Vanderwerf, C. A. Exchange reactions of α-halogenated pyridines. J. Org. Chem. 1951, 16, 1143-1152.
    • (1951) J. Org. Chem , vol.16 , pp. 1143-1152
    • Bradlow, H.L.1    Vanderwerf, C.A.2
  • 30
    • 17044369204 scopus 로고    scopus 로고
    • Asymmetric synthesis of bicyclic β-lactones via the intramolecular, nucleophile-catalyzed aldol lactonization: Improved efficiency and expanded scope
    • Oh, S. H.; Cortez, G. S.; Romo, D. Asymmetric synthesis of bicyclic β-lactones via the intramolecular, nucleophile-catalyzed aldol lactonization: Improved efficiency and expanded scope. J. Org. Chem. 2005, 70, 2835-2838.
    • (2005) J. Org. Chem , vol.70 , pp. 2835-2838
    • Oh, S.H.1    Cortez, G.S.2    Romo, D.3
  • 31
    • 0037421895 scopus 로고    scopus 로고
    • Out of the kitchen
    • Adam, D. Out of the kitchen. Nature 2003, 421, 571-572.
    • (2003) Nature , vol.421 , pp. 571-572
    • Adam, D.1
  • 32
    • 0029078472 scopus 로고
    • Microwave assisted organic reactions
    • Caddick, S. Microwave assisted organic reactions. Tetrahedron 1995, 51, 10403-10432.
    • (1995) Tetrahedron , vol.51 , pp. 10403-10432
    • Caddick, S.1
  • 33
    • 3042733018 scopus 로고    scopus 로고
    • Fatty acid methyl esters synthesis from triglycerides over heterogeneous catalysts in the presence of microwaves
    • Mazzocchia, C.; Modica, G.; Kaddouri, A.; Nannicini, R. Fatty acid methyl esters synthesis from triglycerides over heterogeneous catalysts in the presence of microwaves. Comptes Rendus Chimie 2004, 7, 601-605.
    • (2004) Comptes Rendus Chimie , vol.7 , pp. 601-605
    • Mazzocchia, C.1    Modica, G.2    Kaddouri, A.3    Nannicini, R.4
  • 34
    • 0037025725 scopus 로고    scopus 로고
    • Large scale microwave-accelerated esterification of carboxylic acids with dimethyl carbonate
    • Shieh, W.-C.; Dell, S.; Repic, O. Large scale microwave-accelerated esterification of carboxylic acids with dimethyl carbonate. Tetrahedron Lett. 2002, 43, 5607-5609.
    • (2002) Tetrahedron Lett , vol.43 , pp. 5607-5609
    • Shieh, W.-C.1    Dell, S.2    Repic, O.3
  • 35
    • 0038128281 scopus 로고    scopus 로고
    • BASF's smart ionic liquid
    • Freemantle, M. BASF's smart ionic liquid. C&EN. 2003, 81, 9.
    • (2003) C&EN , vol.81 , pp. 9
    • Freemantle, M.1
  • 37
    • 33947447478 scopus 로고
    • Ionization constants of butylamine, piperidine and triethylamine in methanol
    • Schaefgen, J. R.; Newman, M. S.; Verhoek, F. H. Ionization constants of butylamine, piperidine and triethylamine in methanol. J. Am. Chem. Soc. 1944, 66, 1847-1849.
    • (1944) J. Am. Chem. Soc , vol.66 , pp. 1847-1849
    • Schaefgen, J.R.1    Newman, M.S.2    Verhoek, F.H.3
  • 39
    • 20444492751 scopus 로고    scopus 로고
    • 2O/amine-mediated reduction of alkyl halides: Amine base strength (pKBH+) dependent rate
    • 2O/amine-mediated reduction of alkyl halides: Amine base strength (pKBH+) dependent rate. J. Am. Chem. Soc. 2005, 127, 8340-8347.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 8340-8347
    • Dahlen, A.1    Hilmersson, G.2
  • 40
    • 0000419118 scopus 로고
    • Studies on the iron(II) meso-oxyporphyrin π-neutral radical as a reaction intermediate in heme catabolism
    • Morishima, I.; Fujii, H.; Shiro, Y.; Sano, S. Studies on the iron(II) meso-oxyporphyrin π-neutral radical as a reaction intermediate in heme catabolism. Inorg. Chem. 1995, 34, 1528-1535.
    • (1995) Inorg. Chem , vol.34 , pp. 1528-1535
    • Morishima, I.1    Fujii, H.2    Shiro, Y.3    Sano, S.4
  • 41
    • 0013577889 scopus 로고
    • Nucleophilic substitution at centers other than carbon: Reaction at the chlorine of N-chloroacetanilides with triethylamine as the nucleophile
    • Underwood, G. R.; Dietze, P. E. Nucleophilic substitution at centers other than carbon: reaction at the chlorine of N-chloroacetanilides with triethylamine as the nucleophile. J. Org. Chem. 1984, 49, 5225-5229.
    • (1984) J. Org. Chem , vol.49 , pp. 5225-5229
    • Underwood, G.R.1    Dietze, P.E.2
  • 42
    • 39349083308 scopus 로고
    • A convenient method for the transformation of alcohols to alkyl iodides using 2-fluoropyridinium salt
    • Kobayashi, S.; Tsutsui, M.; Mukaiyama, T. A convenient method for the transformation of alcohols to alkyl iodides using 2-fluoropyridinium salt. Chem. Lett. 1976, 373-374.
    • (1976) Chem. Lett , pp. 373-374
    • Kobayashi, S.1    Tsutsui, M.2    Mukaiyama, T.3
  • 43
    • 0007742883 scopus 로고
    • Optical interconversion of enantiomeric secondary alcohols using 2-fluorobenzothiazolium salt
    • Mukaiyama, T.; Hojo, K. Optical interconversion of enantiomeric secondary alcohols using 2-fluorobenzothiazolium salt. Chem. Lett. 1976, 893-896.
    • (1976) Chem. Lett , pp. 893-896
    • Mukaiyama, T.1    Hojo, K.2
  • 44
    • 33748616485 scopus 로고
    • The kinetics of the α-chymotrypsin-catalyzed hydrolysis of acetyl- and nicotinyl-L- phenylalaninamide in aqueous solutions at 25̊ and pH 7.91
    • Huang, H. T.; Foster, R. J.; Niemann, C. The kinetics of the α-chymotrypsin-catalyzed hydrolysis of acetyl- and nicotinyl-L- phenylalaninamide in aqueous solutions at 25̊ and pH 7.91. J. Am. Chem. Soc. 1952, 74, 105-109.
    • (1952) J. Am. Chem. Soc , vol.74 , pp. 105-109
    • Huang, H.T.1    Foster, R.J.2    Niemann, C.3
  • 45
    • 14544285465 scopus 로고    scopus 로고
    • Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis
    • Boaz, N. W.; Mackenzie, E. B.; Debenham, S. D.; Large, S. E.; Ponasik, J. A. Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis. J. Org. Chem. 2005, 70, 1872-1880.
    • (2005) J. Org. Chem , vol.70 , pp. 1872-1880
    • Boaz, N.W.1    Mackenzie, E.B.2    Debenham, S.D.3    Large, S.E.4    Ponasik, J.A.5
  • 46
    • 0030737815 scopus 로고    scopus 로고
    • Controlled racemization of optically active organic compounds: Prospects for asymmetric transformation
    • Ebbersa, E. J.; Ariaansa, G. J. A.; Houbiersa, J. P. M.; Bruggink, A.; Zwanenburg, B. Controlled racemization of optically active organic compounds: Prospects for asymmetric transformation. Tetrahedron 1997, 53, 9417-9476.
    • (1997) Tetrahedron , vol.53 , pp. 9417-9476
    • Ebbersa, E.J.1    Ariaansa, G.J.A.2    Houbiersa, J.P.M.3    Bruggink, A.4    Zwanenburg, B.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.