Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1999-06-25
2000-07-18
Ambrose, Michael G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
562402, 562468, C07C22936, C07B 5700
Patent
active
060909714
ABSTRACT:
A process for the preparation of optically active phenylcyclohexylglycolate 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.
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 Enantiomers", Acta Chem. Scand. B 40, 601-603 (1986).
Inch et al., "Asymmetric Systhesis: Part III. Stereospecific Synthesis of (R)-2-Hydroxy-2-phenylpropionic (R)-and (S)-2-Cyclohexyl-2-hydroxy-2phenylacetic Acid. Configuration 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., 19-720 (1965).
S.G. Kuznetsov and Z.I. Bobysheva,"Optical Isomers of Some Cholinolytic Substances", J. General Chem. (US (1962).
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 Isometric 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).
Bakale Roger P.
Lopez Jorge L.
McConville Francis X.
Senanayake Chris Hugh
Vandenbossche Charles P.
Ambrose Michael G.
Sepracor Inc.
LandOfFree
Resolution process for cyclohexylphenyl glycolic acid 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 process for cyclohexylphenyl glycolic acid, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Resolution process for cyclohexylphenyl glycolic acid will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2038526