메뉴 건너뛰기




Volumn 22, Issue 1, 2010, Pages 16-23

Diastereomeric resolution of p-chloromandelic acid with (R)-phenylethylamine

Author keywords

Binary melting point phase diagram; Crystal structure; Diastereomeric salt; p chloromandelic acid; Phenylethylamine; Resolution

Indexed keywords

4 CHLOROMANDELIC ACID; MANDELIC ACID; PHENETHYLAMINE; UNCLASSIFIED DRUG;

EID: 75449092835     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20695     Document Type: Article
Times cited : (15)

References (22)
  • 1
    • 75449111860 scopus 로고    scopus 로고
    • Adams AD, Jones AB, Berger ,JP. Preparation of 2-aryloxy-2-arylalkanoic acids for diabetes and lipid disorders. WO2002064094, 2002.
    • Adams AD, Jones AB, Berger ,JP. Preparation of 2-aryloxy-2-arylalkanoic acids for diabetes and lipid disorders. WO2002064094, 2002.
  • 2
    • 75449092489 scopus 로고    scopus 로고
    • Klaus D, Wolfgang S. Optically active amines and their production. WO200138292, 2001.
    • Klaus D, Wolfgang S. Optically active amines and their production. WO200138292, 2001.
  • 3
    • 75449107221 scopus 로고    scopus 로고
    • Deng JG, Wu TF, Cui X, Chen YC, Jiang YZ. Process for preparing optical-purity Fluoxetine. CN1294120A, 2001.
    • Deng JG, Wu TF, Cui X, Chen YC, Jiang YZ. Process for preparing optical-purity Fluoxetine. CN1294120A, 2001.
  • 4
    • 20444431209 scopus 로고    scopus 로고
    • Preparation of (S)-mandelic acids by enantioselective degradation of racemates with a new isolates Pseudomonas Putida ECU1009
    • Huang HR, Xu JH, Xu Y. Preparation of (S)-mandelic acids by enantioselective degradation of racemates with a new isolates Pseudomonas Putida ECU1009. Tetrahedron Asymmetry 2005;16:2113-2117.
    • (2005) Tetrahedron Asymmetry , vol.16 , pp. 2113-2117
    • Huang, H.R.1    Xu, J.H.2    Xu, Y.3
  • 5
    • 75449108017 scopus 로고    scopus 로고
    • Yamaguchi Y, Hamanaka K, Shibuya N. Optical resolution of racemic organic acids using optically active 4-amino-2-methylbutan-1-ol. JP2002030032, 2002.
    • Yamaguchi Y, Hamanaka K, Shibuya N. Optical resolution of racemic organic acids using optically active 4-amino-2-methylbutan-1-ol. JP2002030032, 2002.
  • 6
    • 75449087237 scopus 로고    scopus 로고
    • Honda Y, Nakamura M, Yugawa T. Optical resolution of mandelic acid derivative. JP1221345, 1989.
    • Honda Y, Nakamura M, Yugawa T. Optical resolution of mandelic acid derivative. JP1221345, 1989.
  • 7
    • 0042320405 scopus 로고    scopus 로고
    • Facile resolution of racemic terbutaline and a study of molecular recognition through chiral supramolecules based on enantiodifferentiating self-assembly
    • Liao L, Peng XH, Zhang JH, Yu KB, Cui X, Zhu J, Deng JG. Facile resolution of racemic terbutaline and a study of molecular recognition through chiral supramolecules based on enantiodifferentiating self-assembly. Org Biomol Chem 2003;1:1080-1085.
    • (2003) Org Biomol Chem , vol.1 , pp. 1080-1085
    • Liao, L.1    Peng, X.H.2    Zhang, J.H.3    Yu, K.B.4    Cui, X.5    Zhu, J.6    Deng, J.G.7
  • 8
    • 20444417800 scopus 로고    scopus 로고
    • Influence of (S)-1-phenylethylamine para substitution on the resolution of (+/-)-1,4-benzodioxane-2-carboxylic acid: A crystallographic, theoretical and morphologic approach
    • Marchini N, Bombieri G, Artali R, Bolchi C, Pallavicini M, Valoti E. Influence of (S)-1-phenylethylamine para substitution on the resolution of (+/-)-1,4-benzodioxane-2-carboxylic acid: a crystallographic, theoretical and morphologic approach. Tetrahedron Asymmetry 2005;16:2099-2106.
    • (2005) Tetrahedron Asymmetry , vol.16 , pp. 2099-2106
    • Marchini, N.1    Bombieri, G.2    Artali, R.3    Bolchi, C.4    Pallavicini, M.5    Valoti, E.6
  • 9
    • 0034309254 scopus 로고    scopus 로고
    • Crystal structure-solubility relationships in optical resolution by diastereomeric salt formation of DL-phenylglycine with (1S)-(+)-camphor-10-sulfonic acid
    • Yoshioka R, Hiramatsu H, Okamura K, Tsujioka I, Yamada S. Crystal structure-solubility relationships in optical resolution by diastereomeric salt formation of DL-phenylglycine with (1S)-(+)-camphor-10-sulfonic acid. J Chem Soc Perkin Trans 2 2000;10:2121-2128.
    • (2000) J Chem Soc Perkin Trans 2 , vol.10 , pp. 2121-2128
    • Yoshioka, R.1    Hiramatsu, H.2    Okamura, K.3    Tsujioka, I.4    Yamada, S.5
  • 10
    • 0040673684 scopus 로고    scopus 로고
    • Diastereomeric salts of lactic acid and 1-phenyl-ethylamine, their structures & relative stabilities
    • Langkilde A, Oddershede J, Larsen S. Diastereomeric salts of lactic acid and 1-phenyl-ethylamine, their structures & relative stabilities. Acta Crystallogr Sect B 2002;58:1044-1050.
    • (2002) Acta Crystallogr Sect B , vol.58 , pp. 1044-1050
    • Langkilde, A.1    Oddershede, J.2    Larsen, S.3
  • 11
    • 34047193178 scopus 로고    scopus 로고
    • The role of CH/π interaction in the stabilization of less-soluble diastereomeric salt crystals
    • Saigo K, Kobayashi Y. The role of CH/π interaction in the stabilization of less-soluble diastereomeric salt crystals. Chem Rec 2007;7:47-56.
    • (2007) Chem Rec , vol.7 , pp. 47-56
    • Saigo, K.1    Kobayashi, Y.2
  • 12
    • 39749177077 scopus 로고    scopus 로고
    • Factors determining the pattern of a hydrogen-bonding network in the diastereomeric salts of 1-arylethylamines with enantiopure P-chiral acids
    • Kobayashi Y, Hiroaki H, JIN M, Saigo K. Factors determining the pattern of a hydrogen-bonding network in the diastereomeric salts of 1-arylethylamines with enantiopure P-chiral acids. Chirality 2008;20:577-584.
    • (2008) Chirality , vol.20 , pp. 577-584
    • Kobayashi, Y.1    Hiroaki, H.2    JIN, M.3    Saigo, K.4
  • 13
    • 0000550753 scopus 로고    scopus 로고
    • Systematic study of chiral discrimination upon crystallisation. Part 2. Chiral discrimination of 2-arylalkanoic acids by (1R, 2S)-2-amino-1, 2-diphenylethanol
    • Kinbara K, Kobayashi Y, Saigo K. Systematic study of chiral discrimination upon crystallisation. Part 2. Chiral discrimination of 2-arylalkanoic acids by (1R, 2S)-2-amino-1, 2-diphenylethanol. J Chem Soc Perkin Trans 2 1998;8:1767-1775.
    • (1998) J Chem Soc Perkin Trans 2 , vol.8 , pp. 1767-1775
    • Kinbara, K.1    Kobayashi, Y.2    Saigo, K.3
  • 14
    • 0034236734 scopus 로고    scopus 로고
    • A high-performance, tailor-made resolving agent: Remarkable enhancement of resolution ability by introducing a naphthyl group into the fundamental skeleton
    • Kinbara K, Harada Y, Saigo K. A high-performance, tailor-made resolving agent: remarkable enhancement of resolution ability by introducing a naphthyl group into the fundamental skeleton. J Chem Soc Perkin Trans 2 2000;7:1339-1347.
    • (2000) J Chem Soc Perkin Trans 2 , vol.7 , pp. 1339-1347
    • Kinbara, K.1    Harada, Y.2    Saigo, K.3
  • 15
    • 0010502807 scopus 로고    scopus 로고
    • Chiral discrimination upon crystallization of the diastereomeric salts of 1-arylethylamines with mandelic or p-methoxymandelic acid: Interpretation of the resolution efficiencies on the basis of the crystal structures
    • Kinbara K, Sakai K, Hashimoto Y, Nohira H, Saigo K. Chiral discrimination upon crystallization of the diastereomeric salts of 1-arylethylamines with mandelic or p-methoxymandelic acid: interpretation of the resolution efficiencies on the basis of the crystal structures. J Chem Soc Perkin Trans 2 1996;12:2615-2622.
    • (1996) J Chem Soc Perkin Trans 2 , vol.12 , pp. 2615-2622
    • Kinbara, K.1    Sakai, K.2    Hashimoto, Y.3    Nohira, H.4    Saigo, K.5
  • 16
    • 0032479399 scopus 로고    scopus 로고
    • 2-Naphthylglycolic acid: A tailored resolving agent for p-substituted 1-arylethylamines
    • Kinbara K, Harada Y, Saigo K. 2-Naphthylglycolic acid: a tailored resolving agent for p-substituted 1-arylethylamines. Tetrahedron Asymmetry 1998;9:2219-2222.
    • (1998) Tetrahedron Asymmetry , vol.9 , pp. 2219-2222
    • Kinbara, K.1    Harada, Y.2    Saigo, K.3
  • 19
    • 17844363455 scopus 로고    scopus 로고
    • Highly efficient resolutions of 1, 4-benzodioxane-2-carboxylic acid with para substituted 1-phenylethylamines
    • Bolchi C, Pallavicini M, Fumagalli L. Highly efficient resolutions of 1, 4-benzodioxane-2-carboxylic acid with para substituted 1-phenylethylamines. Tetrahedron Asymmetry 2005;16:1639-1643.
    • (2005) Tetrahedron Asymmetry , vol.16 , pp. 1639-1643
    • Bolchi, C.1    Pallavicini, M.2    Fumagalli, L.3
  • 20
    • 0027285533 scopus 로고
    • Tetrahedron. Racemate resolution via crystallization of diastereomeric salts: Thermodynamic considerations and molecular mechanics calculations
    • Leusen FJJ, Noordik JH, Karfunkel HR. Tetrahedron. Racemate resolution via crystallization of diastereomeric salts: thermodynamic considerations and molecular mechanics calculations. Tetrahedron 1993;49:5377-5396.
    • (1993) Tetrahedron , vol.49 , pp. 5377-5396
    • Leusen, F.J.J.1    Noordik, J.H.2    Karfunkel, H.R.3
  • 22
    • 0006589268 scopus 로고
    • Encoding and decoding hydrogen-bond patterns of organic compounds
    • Etter MC. Encoding and decoding hydrogen-bond patterns of organic compounds. Acc Chem Res 1990;23:120-126.
    • (1990) Acc Chem Res , vol.23 , pp. 120-126
    • Etter, M.C.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.