(3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide

Base Information

Chemical Name:(3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide
CAS No.:1266233-13-9
Molecular Formula:C₂₅H₃₄F₂N₄O₄
Molecular Weight:492.566
Hs Code.:

(3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide

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Chemical Property of (3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide

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Technology Process of (3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide

There total 10 articles about (3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide 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:

: 1266233-10-6
benzyl {(1S)-1-(4,4-difluorocyclohexyl)-2-[(3S,7R,8aR)-3-[(4R)-3,4-dihydro-2H-chromen-4-ylcarbamoyl]-7-hydroxyhexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxoethyl}carbamate

: 1266233-13-9
(3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide

Guidance literature:: With hydrogenchloride; 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; at 20 ℃; for 18h;
DOI:10.1021/jm301674z

Reference yield:

: 873581-24-9
methyl (2S)-{[(benzyloxy)carbonyl]amino}(1,4-dioxaspiro[4.5]dec-8-yl)ethanoate

: 1266233-13-9
(3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: dichloro-acetic acid / tetrahydrofuran; water; acetic acid / 3 h / 30 °C

2.1: diethylamino-sulfur trifluoride / dichloromethane / 1 h / 20 °C

2.2: 5 h / 20 °C

3.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 2 h / 0 - 20 °C

4.1: benzotriazol-1-ol; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 15 h / 20 °C

5.1: hydrogenchloride; hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 18 h / 20 °C

With hydrogenchloride; dichloro-acetic acid; dmap; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; 20% palladium hydroxide-activated charcoal; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm301674z

Reference yield:

: 1241377-38-7
methyl (2S)-{[(benzyloxy)carbonyl]amino}(4-oxocyclohexyl)ethanoate

: 1266233-13-9
(3S,7,8aR)-2-[(2S)-2-amino-2-(4,4-difluorocyclohexyl)acetyl]-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-7-hydroxyoctahydropyrrolo[1,2-a]pyrazine-3-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: diethylamino-sulfur trifluoride / dichloromethane / 1 h / 20 °C

1.2: 5 h / 20 °C

2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 2 h / 0 - 20 °C

3.1: benzotriazol-1-ol; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 15 h / 20 °C

4.1: hydrogenchloride; hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 18 h / 20 °C

With hydrogenchloride; dmap; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; 20% palladium hydroxide-activated charcoal; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm301674z