Heterogeneous synthesis of azepinones from esters

Details Heterogeneous synthesis of azepinones from esters Heterogeneous synthesis of azepinones from esters

1992-09-02

1993-10-05

Rotman, Alan L.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540490, C07D28102

Patent

active

052506800

ABSTRACT:
An amino-acid ester compound can be cyclized into a cyclic amido-carbonyl compound by contacting the amino-acid ester compound in a liquid medium with a heterogeneous acidic ion-exchange substance. For example, 2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)propionic acid, methyl ester, threo form, can be cyclized in an aqueous mixture into cis-2-(4-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one by employing a sulfonated polystyrene-divinylbenzene ion-exchange resin in its acid form, e.g., Dowex.RTM. 50X4-400. at yields exceeding 85 percent of theory, and the product can be used to make diltiazem hydrochloride.

REFERENCES:
patent: 3112554 (1964-02-01), Poos et al.
patent: 3562257 (1971-02-01), Kugita et al.
patent: 3862955 (1975-01-01), Grivas
patent: 4552695 (1985-11-01), Igarashi et al.
patent: 4567175 (1986-01-01), Takeda et al.
patent: 4805580 (1989-02-01), Mohacsi et al.
Akelah "Application of Functionalized polymeric . . . " Chem. Rev. 81 557-587 (1981).
Kugita et al. "Synthesis of 1,5-Benzpthiazepine" Chem. Pharm. Bull 18(10) 2028-2073 (1970).
Mary Friser "Reagents for Organic Synthesis" Wiley & Sons vol. 10, pp. 512-518 (1981).
Morrison and Boyd, "Organic Chemistry, 3rd Edition," Allyn and Bacon, Inc., Boston (1973), pp. 1002-1004.
Khym, "Analytical Ion-Exchange Procedures in Chemistry and Biology, Theory, Equipment, Techniques," Prenice-Hall, Inc., Englewood Cliffs, N.J. (1974), pp. 15 & 62-65.
Ricci et al. "Similarity of the oxidation . . . " J. Biol. Chem. 258 (17) 10511-10517 (1983).
Kugita et al., A Mild and Selective Method of Ester Hydrolysis, Synth. Commun., 19 (3 & 4), pp. 627-631 (1989).
Kohler et al., J. Am. Chem. Soc., 49, pp. 3181-3188 (1927), "An Apparatus for Determining both the Quantity of Gas Evolved and the Amount of Reagent Consumed in Reactions with Methyl Magnesium Iodide".

Affiliated with

Also associated with

Rating

Heterogeneous synthesis of azepinones from esters does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Heterogeneous synthesis of azepinones from esters, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Heterogeneous synthesis of azepinones from esters will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1005296