(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid

Base Information

Chemical Name:(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid
CAS No.:1407162-58-6
Molecular Formula:C₂₄H₂₉N₃O₆
Molecular Weight:455.511
Hs Code.:

Synonyms:(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid

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Chemical Property of (3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid

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Technology Process of (3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid

There total 1 articles about (3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid 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: 73.0%

: 500-22-1
3-pyridinecarboxaldehyde

: 526222-99-1
(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-aminopyrrolidine-3-carboxylic acid

: 1407162-58-6
(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid

Guidance literature:: 3-pyridinecarboxaldehyde; (3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-aminopyrrolidine-3-carboxylic acid; In methanol; at 20 ℃; for 0.5h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 12h;
DOI:10.1021/ja3069648

Reference yield:

: 1407162-58-6
(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid

: 103-71-9
phenyl isocyanate

: C₃₁H₃₂N₄O₆

Guidance literature:: With triethylamine; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1021/ja3069648

Reference yield:

: 1407162-58-6
(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-((pyridin-3-yl)methylamino)pyrrolidine-3-carboxylic acid

: C₄₆H₃₆F₃N₇O₈

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 24 h / 20 °C

2.1: hydrogen bromide / dichloromethane; acetic acid / 1.5 h / 20 °C

3.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere

3.2: 20 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; borane dimethylamine complex / N,N-dimethyl-formamide / 24 h / 20 °C

4.2: 3 h / 20 °C

5.1: chloroform-d1 / 22 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; borane dimethylamine complex; In tetrahydrofuran; chloroform-d1; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/ja3069648