L-Tartaric acid-mediated Isolation of Optically Pure L-Penicillamine from Racemic Penicillamine

Seon Yi Park; Bang Sook Lee; Sung Keon Namgoong

Journal of Industrial and Engineering Chemistry, Vol.8, No.6, 515-518, November, 2002

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L-Tartaric acid-mediated Isolation of Optically Pure L-Penicillamine from Racemic Penicillamine

Seon Yi Park, Bang Sook Lee, and Sung Keon Namgoong^†

Department of Chemistry, Seoul Wonmen's University, Seoul 139-774, Korea

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Optical resolution of the unprotected racemic penicillamine was successfully achieved by L-tartaric acid in methanol/acetic acid. This process based on diastereomeric interaction gave the optically pure L-penicillamine in 80% yield.

Keywords:L-penicillamine;L-tartaric acid;racemic penicillamine;resolution;optical purity

[References]

Weigert WM, Offermanns H, Scherberich P, Angew. Chem.-Int. Edit., 14, 330 (1975)
Asinger AF, Offermanns H, Gluzek AKH, VonBebengurg BW, U.S. Patent, 3,966,752 (1976)
Chandra P, U.S. Patent, 4,847,297 (1989)
Chandra P, Chem. Abstr., 107, 83907 (1987)
Chang MS, Getman DP, Mueller RA, Ottinger JC, Stolzenbach JC, Talley JJ, Vazquez ML, Decrescenzo GA, U.S. Patent, 5,750,648 (1998)
Chang MS, Getman DP, Mueller RA, Ottinger JC, Stolzenbach JC, Talley JJ, Vazquez ML, Decrescenzo GA, Chem. Abstr., 129, 16395 (1998)
Kim SC, Son YC, Choi HI, U.S. Patent, 5,773,468 (1998)
Kim SC, Son YC, Choi HI, Chem. Abstr., 129, 95394 (1998)
duVigneaud V, Holley RW, U.S. Patent, 2,543,358 (1945)
Clarke HT, Johnson JR, Robinson R, The Chemistry of Penicillin, pp. 459-463, Princeton University Press (1949)
Scherberich P, Ger. Patent, 23 62 687 (1975)
Scherberich P, Chem. Abstr., 83, 114924 (1975)
Shiraiwa T, Shinjo K, Maekawa A, Gien., 88, 40 (1996)
Eliel EL, Wilen SH, Doyle MP, Basic Organic Stereochemistry, pp. 209-216, Wiley, New York, the references cited therein (2001)
leCorre M, Hercouet A, Bessieres B, J. Org. Chem., 59, 5483 (1994)
Okuma K, Tanaka Y, Yoshihara K, Ezaki A, Koda G, Ohta H, Hara K, Kashimura S, J. Org. Chem., 58, 5915 (1993)
Shiraiwa T, Kataoka K, Sakata S, Kurokawa H, Bull. Chem. Soc. Jpn., 61, 4158 (1988)
Ogawa T, Tomisawa K, Sota K, Chem. Pharm. Bull., 37, 1609 (1989)
Shiraiwa T, Kataoka K, Sakata S, Kurokawa H, Bull. Chem. Soc. Jpn., 62, 109 (1989)

[Referenced By]

[1] Weigert WM, Offermanns H, Scherberich P, Angew. Chem.-Int. Edit., 14, 330 (1975)

[2] Asinger AF, Offermanns H, Gluzek AKH, VonBebengurg BW, U.S. Patent, 3,966,752 (1976)

[3] Chandra P, U.S. Patent, 4,847,297 (1989)

[4] Chandra P, Chem. Abstr., 107, 83907 (1987)

[5] Chang MS, Getman DP, Mueller RA, Ottinger JC, Stolzenbach JC, Talley JJ, Vazquez ML, Decrescenzo GA, U.S. Patent, 5,750,648 (1998)

[6] Chang MS, Getman DP, Mueller RA, Ottinger JC, Stolzenbach JC, Talley JJ, Vazquez ML, Decrescenzo GA, Chem. Abstr., 129, 16395 (1998)

[7] Kim SC, Son YC, Choi HI, U.S. Patent, 5,773,468 (1998)

[8] Kim SC, Son YC, Choi HI, Chem. Abstr., 129, 95394 (1998)

[9] duVigneaud V, Holley RW, U.S. Patent, 2,543,358 (1945)

[10] Clarke HT, Johnson JR, Robinson R, The Chemistry of Penicillin, pp. 459-463, Princeton University Press (1949)

[11] Scherberich P, Ger. Patent, 23 62 687 (1975)

[12] Scherberich P, Chem. Abstr., 83, 114924 (1975)

[13] Shiraiwa T, Shinjo K, Maekawa A, Gien., 88, 40 (1996)

[14] Eliel EL, Wilen SH, Doyle MP, Basic Organic Stereochemistry, pp. 209-216, Wiley, New York, the references cited therein (2001)

[15] leCorre M, Hercouet A, Bessieres B, J. Org. Chem., 59, 5483 (1994)

[16] Okuma K, Tanaka Y, Yoshihara K, Ezaki A, Koda G, Ohta H, Hara K, Kashimura S, J. Org. Chem., 58, 5915 (1993)

[17] Shiraiwa T, Kataoka K, Sakata S, Kurokawa H, Bull. Chem. Soc. Jpn., 61, 4158 (1988)

[18] Ogawa T, Tomisawa K, Sota K, Chem. Pharm. Bull., 37, 1609 (1989)

[19] Shiraiwa T, Kataoka K, Sakata S, Kurokawa H, Bull. Chem. Soc. Jpn., 62, 109 (1989)