((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

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Chemical Name:((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester
CAS No.:183595-83-7
Molecular Formula:C₂₈H₃₄N₄O₄
Molecular Weight:490.602
Hs Code.:

Synonyms:((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

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Chemical Property of ((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

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Technology Process of ((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

There total 5 articles about ((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: (S)-N-(4-cyanophenethyl)pyrrolidine-2-carboxamide hydrochloride

: 18942-49-9
Boc-D-Phe-OH

: 183595-83-7
((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

Guidance literature:: (S)-N-(4-cyanophenethyl)pyrrolidine-2-carboxamide hydrochloride; Boc-D-Phe-OH; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 0.166667h;

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1016/j.bioorg.2020.103856

Reference yield:

: 105-07-7
4-cyanobenzaldehyde

: 183595-83-7
((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) NaH, 2.) H₂, 3.) LiOH, 4.) DPPA, TEA, 5.) HCl / 2.) 5percent Pd/BaSO₄ / 1.) THF, 2.) toluene, 3.) p-dioxane, H₂O, 4.) t-BuOH, reflux, 5.) EtOAc

2: EDC, HOBT, DIEA / CH₂Cl₂

With hydrogenchloride; lithium hydroxide; TEA; diphenyl-phosphinic acid; hydrogen; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; Pd-BaSO₄; In dichloromethane;
DOI:10.1016/0960-894X(96)00442-8

Reference yield:

: 15761-39-4,59433-50-0
1-(tert-butoxycarbonyl)-L-proline

: 183595-83-7
((R)-1-Benzyl-2-{(S)-2-[2-(4-cyano-phenyl)-ethylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h

1.2: 16 h / 20 °C

2.1: hydrogenchloride / methanol; water / 3 h / 0 - 20 °C

3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.17 h

3.2: 16 h / 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bioorg.2020.103856