Synthesis of optically active trans 4-cyclohexyl-L-proline as an intermediate product in the preparation of fosinopril.
A nine-step synthesis of trans 4-cyclohexyl-L-proline has been developed on a laboratory scale. The product is an intermediate in the preparation of fosinopril--an effective hypotensive drug. The total yield of the synthesis was 25%. The final product was 99.7% pure. Analytical methods were developed for each step of the synthesis (HPLC, TLC, IR, 1H-NMR, 13C-NMR, GC-MS, [alpha]D).
Kalisz
Dorota
D
Industrial Chemistry Research Institute, 8 Rydygiera Str, 01-793 Warsaw, Poland.
Dabrowski
Zbigniew
Z
Kakol
Barbara
B
Bełdowicz
Maria
M
Obukowicz
Bozenna
B
Kamiński
Jarosław
J
D000959:Antihypertensive Agents / Q000032:analysis / Q000138:chemical synthesis / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D017328:Fosinopril / Q000032:analysis / Q000138:chemical synthesis* / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D011392:Proline / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013678:Technology, Pharmaceutical / Q000379:methods
D000959:Antihypertensive Agents; D011392:Proline; D017328:Fosinopril