(3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-1-carboxylate
CAS No.:1428243-41-7
Molecular Formula:C₂₈H₂₉N₅O₅S
Molecular Weight:547.635
Hs Code.:

Synonyms:(3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-1-carboxylate

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Chemical Property of (3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-1-carboxylate

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Technology Process of (3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-1-carboxylate

There total 9 articles about (3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-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: 96.0%

: 1428243-40-6
(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-methylpyrrolidine-1-carboxylate

: 1428243-41-7
(3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-1-carboxylate

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

Reference yield:

: 261896-27-9
(cis)-ethyl 1-benzyl-4-methylpyrrolidine-3-carboxylate

: 1428243-41-7
(3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: water; hydrogenchloride / 15 h / Reflux

2.1: sodium hydroxide; hydrogen; hydrogenchloride; 20% palladium hydroxide on charcoal / water / 16 h / 50 °C / 1551.49 Torr / pH Ca. 2.5

3.1: sodium hydroxide / water / pH Ca_. 11

3.2: 6 h / pH Ca_. 10 - Ca_. 12

3.3: pH Ca_. 2 - Ca_. 3

4.1: acetonitrile / 16 h

5.1: hydrogenchloride / water; diethyl ether

5.2: 3 h

6.1: tetrahydrofuran; acetonitrile / 2 h / 0 - 10 °C

6.2: 1.5 h / 10 °C

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h

7.2: 2 h / 0 - 20 °C

8.1: trifluoroacetic acid / dichloromethane / 48 h / 20 °C / Inert atmosphere

With hydrogenchloride; 20% palladium hydroxide on charcoal; water; hydrogen; sodium hydride; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

Reference yield:

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

: 1428243-41-7
(3S,4R)-benzyl 3-methyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)acetyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h

1.2: 2 h / 0 - 20 °C

2.1: trifluoroacetic acid / dichloromethane / 48 h / 20 °C / Inert atmosphere

With sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; mineral oil;