Process and intermediates for (s)-.alpha.-amino-1-carboxycyclope

Details Process and intermediates for (s)-.alpha.-amino-1-carboxycyclope Process and intermediates for (s)-.alpha.-amino-1-carboxycyclope

1998-01-23

1999-09-07

Barts, Samuel

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

Organic compounds

Carboxylic acid esters

562504, 558432, C07C 6974, C07C 6106

Patent

active

059489359

ABSTRACT:
Disclosed herein is a process for preparing (S)-.alpha.-amino-1-carboxycyclopentaneacetic acid which is a useful intermediate for preparing peptidomimetic inhibitors of herpes viral ribonucleotide reductase. The process comprises the preparation of the key intermediate ##STR1## and its subsequent conversion to the desired product.

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Moss et al., An Enatioselective . . . Scale, Synthesis-J. of Synthetic Org. Chem., No. 1, pp. 32-34, Jan. 1997.
Chang, L.L. et al., "Substituted Penta-and Hexapeptides as Potent Inhibitors of Herpes Simplex Virus Type 2 Ribonucleotide Reductase," Bioorganic Med. Chem. Lett. 2(10):1207-1212 (1992).
Gaudreau, P. et al., "Synthesis and Inhibitory Potency of Peptides Corresponding to the Subunit 2 C-Terminal Region of Herpes Virus Ribonucleotide Reductase," J. Med. Chem. 33(2):723-730 (1990).
Liuzzi, M. et al., "A potent peptidomimetic inhibitor of HSV ribonucleotide reductase with antiviral activity in vivo," Nature 372:695-698 (1994).
Moss, N. et al., "Peptidomimetic Inhibitors of Herpes Simplex Virus Ribonucletide Reductase with Improved in Vivo Antiviral Activity," J. Med. Chem. 39(21):4173-4180 (Oct. 1996).
Moss, N. et al., "Inhibition of Herpes Simplex Virus Type 1 Ribonucleotide Reductase by Substituted Tetrapeptide Derivatives," J. Med. Chem. 36(20):3005-3009 (1993).
Moss, N. et al., "Herpes Simplex Virus Ribonucleotide Reductase Subunit Association Inhibitors: the Effect and Conformation of .beta.-Alkylated Aspartic Acid Derivatives," Bioorganic Med. Chem. 2(9):959-970 (1994).
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