Process for preparing benzothiazepine derivatives

Details Process for preparing benzothiazepine derivatives Process for preparing benzothiazepine derivatives

1994-01-19

1995-12-05

Berch, Mark L.

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

Organic compounds

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

544 59, 544160, 544399, 546221, 5483355, 5483751, 548561, 548569, 560 17, 562431, C07D28110, C07D29514, C07B 4500

Patent

active

054730660

ABSTRACT:
Process for stereoselectivity preparing a cis-form of 5-(aminoalkylamino)-1,5-benzothiazepine derivative represented by formula (VI): ##STR1## is provided, said process comprising carrying out a stereoselective addition reaction of an o-(aminoalkylamino) thiophenyl derivative with a trans-substituted glycidic ester at an elevated temperature in a nonpolar solvent in the presence of a divalent or trivalent iron ion to prepare a threo-form intermediate, hydrolyzing the ester group of said intermediate, acetylating the hydroxyl group of said hydrolyzed compound, and subjecting said acetylated compound to a ring closure reaction to obtain the objective compound (VI).

REFERENCES:
Inoue, J. Med Chem 34, 675-687 (1991).
Nippon Chemical Co., Ltd. Chemical Abstracts, vol. 104, No. 11, 17 Mar. 1986 Abstract No. 88616e JP-A-60 146 884.
Higashigawa, Chemical Abstracts, vol. 101, No. 21, 19 Nov. 1984 Abstract No. 191353d JP-A-59 110 668.
Higashigawa, Chemical Abstracts, vol. 101, No. 19 5 Nov. 1984 Abstract No. 171294g JP-A-59 110 685.
Tanabe Seiyaku Co., Ltd., Chemical Abstracts, vol. 96, No. 5 1 Feb. 1982 Abstract No. 34905w JP-A-81 108 685.
Hashiyama et al., J. Chem., Soc. Perkin Trans. I 1984, pp. 1725-1732.
Hashiyama et al., J. Chem. Soc. Perkin Trans. I 1985, pp. 421-427.

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