Synthesis of optically active cyclohexylphenylglycolate esters

Details Synthesis of optically active cyclohexylphenylglycolate esters Synthesis of optically active cyclohexylphenylglycolate esters

1998-12-15

2000-10-31

Ambrosse, Michael G.

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

Organic compounds

Carboxylic acid esters

552 10, 560 57, C07C21306, C07C21920

Patent

active

061405299

ABSTRACT:
A process for the preparation of optically active cyclohexylphenylglycolate esters is described. The process utilizes carboxylic acid activation to couple (R)- or (S)-cyclohexylphenylglycolic acid (CHPGA) with 4-N,N-diethylamino butynol or other propargyl alcohol derivatives. The preparation of the hydrochloride salt is also described. In addition, a resolution process employing tyrosine methyl ester enantiomers for preparing a single enantiomer of CHPGA from racemic CHPGA is disclosed.

REFERENCES:
patent: 2837525 (1958-06-01), Ruddy et al.
patent: 3176019 (1965-03-01), Campbell et al.
patent: 5036098 (1991-07-01), Kimura et al.
Barlow et al., "Studies on the Stereospecificity of Closely Related Compounds Which Block Postganglionic Acetylcholine Receptors in the Guinea-Pig Ileum", J. Medic. Chem. 16, 439-446 (1973).
L. Schjelderup and A.J. Aasen, "The Absolute Configuration of Oxyphencyclimine, a Parasympatholytic Drug, of Both Enantionmers", Acta Chem. Scand. B 40, 601-603 (1986).
Inch et al., "Asymmetric Synthesis: Part III. Stereospecific Synthesis of (R)-2-Hydroxy-2-phenylpropionic (R)-and (S)-2-Cyclohexyl-2-hydroxy-2-phenylacetic Acid. Configurational Relationship between (R)(-)-2-Hydroxy-2-phenylpropionic Acid and (S)(+)-2-Phenylpropionic Acid", J. Chem. Soc. (C), 1693-1699 (1968).
Majewski et al., "Anticholinergic Agents. Esters of 4-Dialkyl- (or 4-Polymethylene-) amino-2-butynols", J. Chem. Soc., 720 (1965).
S.G. Kuznetsov and Z.I. Bobysheva, "Optical Isomers of Some Cholinolytic Substances", J. General Chem. (USSR) (1962) 32 3707.
Take et al., "Agents for the Treatment of Overactive Detrusor.III. Synthesis and Structure-Activi Relationships of N-(4-Amino-2-butynyl)acetamide Derivatives", Chem. Pharm. Bull., 40 1415-1423 (1992).
K.G. Feitsma, "Enantiomeren Van Oxyfenoniumbromide", Pharm. Weekbl. 124, 383-387 (1989).
Atkinson et al., "Parasympatholytic (Anticholinergic) Esters of the Isomeric 2-Tropanols. 1. Glycolate", J. Med. Chem. 20, 1612-1617 (1977).
Kachur et al., "R and S Enantiomers of Oxybutynin: Pharmacological Effects in Guinea Pig Bladder and Intestine", J. Pharmacol. Exp. Ther., 247, 867-872 (1988).

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