Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its con

Details Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its con Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its con

1998-10-14

2000-02-15

Trinh, Ba K.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 27, 560 39, 560 42, 560 53, 564165, 564167, C07C23102, C07C23118, C07C23120, C07C20900

Patent

active

060255161

ABSTRACT:
The present invention provides an efficient route to the C-13 side chain of the anti-cancer drug paclitaxel (TAXOL) and its analogs. The process includes the resolution of racemic erythro 2-hydroxy-3-amino-3-phenylpropionamide by diastereomeric crystallization and its conversion via various intermediates to the threo-ethylester and threo-methylester isomers.

REFERENCES:
patent: Re34277 (1993-06-01), Denis et al.
patent: 4924011 (1990-05-01), Denis et al.
patent: 5015744 (1991-05-01), Holton
patent: 5136060 (1992-08-01), Holton
patent: 5175315 (1992-12-01), Holton
patent: 5229526 (1993-07-01), Holton
patent: 5292921 (1994-03-01), Correa et al.
patent: 5294737 (1994-03-01), Ojima
patent: 5336785 (1994-08-01), Holton
patent: 5602272 (1997-02-01), Li et al.
patent: 5681970 (1997-10-01), Didier et al.
patent: 5684168 (1997-11-01), Duchesne et al.
patent: 5684175 (1997-11-01), Sisti et al.
patent: 5686616 (1997-11-01), Tani et al.
patent: 5726346 (1998-03-01), Denis et al.
Dennis, Jean-Noel et al., "An Efficient, Enantioselective Synthesis of the Taxol Side Chain", J. Org. Chem. 51, 46-50 (1986).
Honig, H. et al., "Chemo-Enzymatic Synthesis of all Isomeric 3-Phenylserines and -Isoserines", Tetrahedron vol. 46, No. 11, pp. 3841-3850, (1990).

Affiliated with

Also associated with

Rating

Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its con does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its con, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Resolution of 2-hydroxy-3-amino-3-phenylpropionamide and its con will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1907206