Studies on Angiotensin Converting Enzyme Inhibitors. V. The Diastereoselective Syntheis of 2-Oxomidazolidine Derivatives
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概要
- 論文の詳細を見る
A diastereoselective syntesis of imidapril (1), which is under clinical study as an antihypertensive drug based on its angiotensin converting enzyme (ACE)-inhibitory activity, was established. N-Alkylation of (2S)-2-amino-4-phenylbutyric acid ester (12) with 3-((2R)-2-methane or toluenesulfonyloxypropionyl)-2-oxoimidazolidine derivative (11) diastereoselectively proceeded in an SN2 fashion to afford tert-butyl (4S)-3-[(2S)-2-[N-[(1S)-1-ethoxycarbonyl)-3-phenylpropyl]amino]propionyl]-1-methyl-2-oxoimidazolidine-4-carboxylate (13), a precursor of 1. Alternatively, benzyl (2S)-2-[N-(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propionate (15), which is the key building block of 13,was synthesized by teh same strategy. This procedure was also applied to the synthesis of enalapril.
- 公益社団法人日本薬学会の論文
- 1991-06-25
著者
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山岸 正文
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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山岸 正文
Pharmaceutical Technics Division, Tanabe Seiyaku Co., Ltd.,
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西本 茂
Pharmaceutical Technics Division, Tanabe Seiyaku Co., Ltd.,
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窪田 均
Research Laboratory Of Applied Biochemistry:tanabe Seiyaku Co. Ltd.
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沼波 憲一
Research Laboratory Of Applied Biochemistry:tanabe Seiyaku Co. Ltd.
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窪田 均
Reserch Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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沼波 憲一
Reserch Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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林 公明
Reserch Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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西本 茂
Pharmaceutical Technics Division Tanabe Seiyaku Co. Ltd
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林 公明
Research Laboratory Of Applied Biochemistry:tanabe Seiyaku Co. Ltd.
関連論文
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- Quinazolin-2-ones Having a Spirohydantoin Ring. III. A General and Efficient Synthesis of 3'-Substituted Spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2', 5(3'H)-triones
- Quinazolin-2ones Having a Spirohydantoin Ring. II. Synthesis of Several Spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2', 5(3'H)-triones via 5-Hydroxyhydantoin Derivatives
- Quinazolin-2-ones Having a Spirohydantoin Ring.I. : Synthesis of Spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2', 5'-trione by Reaction of 1-Carbamoylisatin with Uera or Guanidine
- Studies on Angiotensin Converting Enzyme Inhibitors. VI. Synthesis and Angiotensin Converting Enzyme Inhibitory Activities of the Dicarboxylic Acid Derivative of Imidapril and Its Diastereoisomers
- Studies on Iodinated Compounds. I. Improved Procedure for Preparation of Monoiodohistidine
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- Studies on Angiotensin-converting Enzyme Inhibitors. I. Syntheses and Angiotensin-converting Enzyme Inhibitory Activity of 2-(3-Mercaptopropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Derivatives
- A NEW TRANSFORMATION OF OXAZOLEACETATES INTO β-AMINOPYPPOLES
- Studies on Angiotensin Converting Enzyme Inhibitors. V. The Diastereoselective Syntheis of 2-Oxomidazolidine Derivatives
- The Practical Resolution of (2RS, 3RS)-2-HYdroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic Acid, a Key Intermediate for Diltiazem, with L-Lysine