(3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid

Base Information

• Chemical Name: (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid
• CAS No.: 1266229-00-8
• Molecular Formula: C₂₅H₄₂N₄O₆
• Molecular Weight: 494.632
• Mol file: 1266229-00-8.mol

Synonyms:(3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid

Chemical Property of (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid

There total 7 articles about (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-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:

methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate (1266228-99-2) → (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid (1266229-00-8)

Guidance literature:

methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate; With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20 ℃; for 3h;

With hydrogenchloride; In tetrahydrofuran; water; Product distribution / selectivity;

Reference yield:

methyl (3S,8aR)-2-benzyloctahydropyrrolo[1,2-a]pyrazine-3-carboxylate (1266228-97-0) → (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid (1266229-00-8)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol / 10 h / 20 °C

2: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; 4-methyl-morpholine / tetrahydrofuran / 4 h / 0 - 20 °C

3: lithium hydroxide monohydrate / tetrahydrofuran / 3 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; methanol;

DOI:10.1021/jm301674z

Reference yield:

methyl (3S,8aR)-octahydropyrrolo[1,2-a]pyrazine-3-carboxylate dihydrochloride → (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylic acid (1266229-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; 4-methyl-morpholine / tetrahydrofuran / 4 h / 0 - 20 °C

2: lithium hydroxide monohydrate / tetrahydrofuran / 3 h / 20 °C

With 4-methyl-morpholine; lithium hydroxide monohydrate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran;

DOI:10.1021/jm301674z

upstream raw materials:

methyl (3S,8aR)-2-[(2S)-2-{[N-(tert-butoxycarbonyl)-N-methyl-L-alanyl]amino}-2-cyclohexylacetyl]octahydropyrrolo[1,2-a]pyrazine-3-carboxylate

D-pyrrolidone-5-carboxylic acid

(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetic acid

(R)-5-oxopyrrolidine-2-carboxylic acid benzylamide

Downstream raw materials:

C₃₂H₄₉N₅O₅

C₃₈H₅₃N₅O₅

tert-buty l[(1S)-2-({(1S)-1-cyclohexyl-2-oxo-2-[(3S,8aR)-3-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl]hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]ethyl}amino)-1-methyl-2-oxoethyl]methylcarbamate

tert-butyl [(1S)-2-({(1S)-1-cyclohexyl-2-[(3S,8aR)-3-[(4R)-3,4-dihydro-2H-cromen-4-ylcarbamoyl] hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-oxoethyl}amino)-1-methyl-2-oxoethyl]methylcarbamate