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Please login or sign up for a free trial to access the full content. Synthesis of l-2-Amino-3-(2-oxocyclopentyl)propanoic Acid

DOI: 10.1055/sos-SD-214-00283

Slomka, C.; Engel, U.; Syldatk, C.; Rudat, J.Science of Synthesis: Biocatalysis in Organic Synthesis, (20151398.

Substituted N-carbamoylglycine derivatives are interesting chemical building blocks for several active pharmaceutical ingredients. Hydantoins with substituents such as acyloxy or acylsulfanyl groups, a cyclic alkene,[‌143‌] or an (oxocycloalkyl)methyl moiety[‌144‌] are all utilized as starting materials for the synthesis of enantiomerically pure α-amino acids.[‌24‌] For example, hydrogenation of l-2-amino-3-(2-oxocyclopentyl)propanoic acid (l-27) gives an intermediate in the synthesis of the angiotensin-converting enzyme (ACE) inhibitor ramipril (see Scheme 15, Section The synthesis of 5-[(2-oxocyclopentyl)methyl]hydantoin (25), the substrate for the synthesis of enantiomerically pure l-2-amino-3-(2-oxocyclopentyl)propanoic acid (l-27), is accomplished from easily accessible starting compounds (Scheme 20).[‌135‌]

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Meeee Meeeeeeee e-α-Meeee Meee ee (%) Meeeee (%) Mee
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Meeee eeeeeeeeee eee eeeeeeee 8-(eeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeee (88; 8.88 e, 88.8 eeee) ee MMM (88 eM), eee eeeeeee eee eeeee eeeeeeee ee e eeee ee Me8M (8.88 e, 88.8 eeee) eee 8-eeeeeeeeeeeeeeeeeeee-8-eee (8.88 e, 88.8 eeee) ee MMM (88 eM) ee 88 °M eee ee eeeeeeee eeeeee eeee ee. 88 eee. Mee eeeeeeeeee eee eeeeeeee eeeee 88 e eeeeeeee ee eee eeeeee-eeeeee eeeeeee ee 88 °M. M8M (8 eM) eee eeee eeeee ee MMe (8 eM) eeee eeeee eee eee eeee eee eeeeeee eee 88 eee. Meee, eee eeeeeee eee eeeeeee (Meeeeeeee, 88 °M), M8M (88 eM) eee eeeee, eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeee eee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee (Meeeeeeee, 88 °M) ee eeee 8-eeeeee-8-[(8-eeeeeeeeeeeeee)eeeeee]eeeeeeeee (88), eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeeeee, eeeeeee eeeeeeee); eeeee: 8.88 e (88%); 8:8 eeeeeee ee eeeeeeeeeeeee.

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Mee eeeeeeeeeee M. eeee eeeee eeee eeeee ee 8eMM eeeeee (888 eM) eeeeeeeeee eeeeeeeeee (88 µe · eM−8) eee MeMe8 ee MeMe8 (8 eM). Meeee 88–88 e ee eeeeeeeeeee ee 88 °M eee 888 eee, eee eeeee eeee eeeeeeeee ee eeeeeeeeeeeeee (8888 eee, 8 °M, 88 eee). Meee, eee eeee eeeeee eee eeeeeeeeeee ee 8.8 M Meee-MMe (8 eM; eM 8.8) eee eeeeeeeeeee (8888 eee, 8 °M, 88 eee). Mee eeeeeeeeeeeeeeeee, eee eeee eeeeee (8.8 e) eee eeeee ee e,e-8-[(8-eeeeeeeeeeeeee)eeeeee]eeeeeeeee (e,e-88; 8.8 e, 8.8 eeee) ee 8.8 M Meee-MMe eeeeee (8 eM; eM 8.8). 8.8 M MeMe8 eeee (88 µM) eee eeeee eee eee eeeeeee eee eeeeeeeee ee 88 °M eeeeeeeee. Meeee eeeeeeeeeeeeee ee ee, eee eeeeeeeeeee eee eeeeeeee (8.88-µ eeeeee); eeeee: 88%, M8: >88% ee (e-eeeeeeeeeeeee); M8: eeeeeeeee eeeeeeeeeeeee.