(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

Base Information

Chemical Name:(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate
CAS No.:1428243-27-9
Molecular Formula:C₃₄H₃₉N₅O₇S
Molecular Weight:661.779
Hs Code.:

Synonyms:(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:: >95% ^*data from raw suppliers

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Technology Process of (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

There total 38 articles about (3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate 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: 60.0%

: 1201187-44-1
N-(5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazin-2-yl)carbamic acid tert-butyl ester

: 1428243-26-8
(3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate

: 1428243-27-9
(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

Guidance literature:: N-(5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazin-2-yl)carbamic acid tert-butyl ester; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 4h;

(3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 1h;

Reference yield:

: (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid

: 1428243-27-9
(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 1,1'-carbonyldiimidazole

2: lithium bromide; toluene-4-sulfonic acid

3: sodium hydride / N,N-dimethyl-formamide

With sodium hydride; toluene-4-sulfonic acid; 1,1'-carbonyldiimidazole; lithium bromide; In N,N-dimethyl-formamide;
DOI:10.1358/dof.2018.043.10.2849626

Reference yield:

: 1-benzyloxycarbonyl-4-ethyl-2,5-dihydropyrrole-3-carboxylic acid ethyl ester

: 1428243-27-9
(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium hydroxide / water; tetrahydrofuran / 50 °C

2: hydrogen; triethylamine; Ru[(S)-SegPhos](OAc)₂ / methanol / 80 °C

3: 1,1'-carbonyldiimidazole

4: lithium bromide; toluene-4-sulfonic acid

5: sodium hydride / N,N-dimethyl-formamide

With Ru[(S)-SegPhos](OAc)₂; hydrogen; sodium hydride; toluene-4-sulfonic acid; triethylamine; 1,1'-carbonyldiimidazole; lithium bromide; sodium hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1358/dof.2018.043.10.2849626