Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
1.4.5.4.1.2.5 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 1.4.5.4.1.2). 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]

Meeeee 88 Meeeeeeee ee 8-[(8-Meeeeeeeeeeeee)eeeeee]eeeeeeeee eeee e-8-(Meeeeeeeeeeee)eeeeeeeee[‌888‌]

Mee eeeeeeeeee eeeeeeeeeee 8-[(8-eeeeeeeeeeeeee)eeeeee]eeeeeeeee (88) ee eeeeeeeee eeee eee eeeeeeeeeeeee e-eeeee eeee, e-8-eeeee-8-(8-eeeeeeeeeeeeee)eeeeeeeee eeee (e-88) eee M-eeeeeeeeeeeeee eeee e-88, eeeee e eeeee-eeee eeeeeeee eeeeee ee M. eeee MM888 eeeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee eeee Meeeeeeeeeee eeeeeeeee MMM 8888, e-M-eeeeeeeeeeee eeee Meeeeeee eeeeeeeeeeeeeeeeee MMMM888, eee eeeeeeeee eeeeeeee eeee Meeeeeeeeeeee eeeeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeee ee e-8-Meeee-8-(8-eeeeeeeeeeeeee)eeeeeeeee Meee eeee e,e-8-[(8-Meeeeeeeeeeeee)eeeeee]eeeeeeeee Meeee Meeeeeeee Meeeeeee, Meeeeeeeeeee, eee e-M-Meeeeeeeeeee[‌888‌]

Meeeeeeee eeee e-8-eeeee-8-(8-eeeeeeeeeeeeee)eeeeeeeee eeee (e-88) ee eeeeeeeeeee eeeee e eeeee-eeee eeeeeeeeeeee eeeeee eeee e eeeeeeeeee ee 88% eee 88% ee. Meeee eeee eeeeeeee eeee eeeeeeeeeee ee e eeeeee eeeeeeee eee eee eeee eeeeeeeeee eeeeeeee, eee eeee eeeeeeeeee, eeee eeeeeee eeee eeeeee ee eee eeee eeeeeee, ee eeeeeeeeee.

Meeeeee eeeeeeeee eee eee eeeeeeeee eee eeeeeeeeeee ee eeeee 8-eeeeeeeeeee eeeeeeeeee eee eee eeeeeeeeee ee eeeeeeeee eeee α-eeeee eeeee eeee eeee eeeeeeeee eee eeeeeeee (Meeee 8).

Meeee 8 Meeeeeeeee eee Meeeeeeee Meeeeeeee Meee α-Meeee Meeee Meeee Meeeeeeee Meeeeeee, Meeeeeeeeeee, eee e-M-Meeeeeeeeeee[‌88‌,‌888‌,‌888‌]

Meeee Meeeeeeee e-α-Meeee Meee ee (%) Meeeee (%) Mee
8 88.8 88 [‌88‌]
8 88.8 e.e. [‌88‌]
8 88 88 [‌88‌,‌888‌]
8 88 e.e. [‌88‌,‌888‌]
8 88 e.e. [‌88‌]

e e.e. = eee eeeeeeeeee.

Mee e-α-eeeee eeeee e-8-eeeee-8-(8-eeeeeeeeeeeee)eeeeeeeee eeee (Meeee 8, eeeee 8) eee e-8-eeeee-8-(8-eeeeeeeeeee-8-eeee)eeeeeeeee eeee (eeeee 8), eee eeeeeee, eee eeeeeeeeeee eeeeeeeee eee eeeeeeeeeeee ee eee eeeeeeeeeeeeee eeeeeeee. Meee eeeee ee eeeeeeeeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeee-eeeeeeeeee eeeeee (MMM) eeeeeeeee eeeeeeeeeee (eee Meeeee 88).

Meeeeeeeeeee Meeeeeeee

e,e-8-[(8-Meeeeeeeeeeeee)eeeeee]eeeeeeeee (e,e-88); Meeeeee Meeeeeeee:[‌888‌]

Meeee eeeeeeeeee e-8-(eeeeeeeeeeeee)eeeeeeeee (88; 88.8 e, 888 eeee) ee eeeee MeMM (888 eM), eee eeeeeee eee eeeeee ee 88 °M eee eeee eeeeeeee (88.8 e, 8.88 eee) eee eeeee eee e eeeeeeeeeee eeee eeeeee. Meeeee eeeeeeee (88.8 e, 8.88 eee) eee eeeee eeeeeeee eeee 8 e ee eeee eee eeeeeeeeeee ee 88 °M. Meeeeeeeeeee, eee eeeeeee eee eeeeeee ee eeee ee ee 88 °M eeeeee eeeee 88 eee eee e eeeeeeeeeee eeeeee. Meeee ee. 88 e, eeee eee eeeeeeeeee eeeeee eeeeee eeeeeeeeeee eee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeeeeeeee (Meeeeeeee, 88 °M) eee ee e eeeeee eeee eeeeee eeeeee. Meeee eee eeeeeeee ee e-MeMMe (888 eM) eee eeeeeeee eee 88 eee, eeee eeeee (eeeeeeeeee eeeeeeee) eeeeeeeeeeee eee ee eee eeeeeeeee ee e eeeeee ee eeeeeee. Meeeeeeeee e-MeMMe (888 eM) eee eeee ee eeee eee eeeeeeeee eeee, eeeee eee eeeeeeeee. Mee eeeeee eeeeee eeeeeeeeee 8-(eeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeee (88) eee eeeeeeeeeeee (Meeeeeeee, 88 °M) ee e eeeee eee; eeeee: 88.8 e (88%); eeeeee: 88%.

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.

8-Meeeee-8-[(8-eeeeeeeeeeeeee)eeeeee]eeeeeeeee (88; 8.88 e, 8.88 eeee) eee eeeeeeeee ee 8 M ee MMe eee eeeeeee eee 88 e ee 88 °M. Meeee eeeeeee eee eeeeeee ee 88 °M, ee eee eeeeeeeee eeee Me8M (88 eM). Mee eeeeeee eeeee eee eeeeeeeeeeee (Meeeeeeee, 88 °M) eee eee eeeeeee eeeee eee eeeeeeeee. Meeeeeeeeeee, e eeeeeeee eeeee ee e,e-8-[(8-eeeeeeeeeeeeee)eeeeee]eeeeeeeee (e,e-88) eee eeeeee; eeeee: 8.88 e (88%); eeeeeee ee eeeeeeeeeeeee.

e-8-Meeee-8-(8-eeeeeeeeeeeeee)eeeeeeeee Meee (e-88); Meeeeee Meeeeeeee Meeee Meeeeeeeeee M. eeee eeee Meeeeeeeeee Meeeeee:[‌888‌]

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.

References


Cookie-Einstellungen