Pyrazine-2-carboxylic acid ((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-hydroxy-3-oxo-3-pyrrolidin-1-yl-propylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butyl)-amide

Base Information

• Chemical Name: Pyrazine-2-carboxylic acid ((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-hydroxy-3-oxo-3-pyrrolidin-1-yl-propylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butyl)-amide
• CAS No.: 676265-55-7
• Molecular Formula: C₃₅H₅₇N₇O₆
• Molecular Weight: 671.881

Synonyms:

Chemical Property of Pyrazine-2-carboxylic acid ((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-hydroxy-3-oxo-3-pyrrolidin-1-yl-propylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pyrazine-2-carboxylic acid ((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-hydroxy-3-oxo-3-pyrrolidin-1-yl-propylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butyl)-amide

There total 9 articles about Pyrazine-2-carboxylic acid ((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-hydroxy-3-oxo-3-pyrrolidin-1-yl-propylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butyl)-amide 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:

Boc-Leu-ONSu (3392-09-4) → Pyrazine-2-carboxylic acid ((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-hydroxy-3-oxo-3-pyrrolidin-1-yl-propylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butyl)-amide (676265-55-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / DIEA / dimethylformamide / 8 h / 0 - 20 °C

2: 95 percent / TFA / CH₂Cl₂

3: 79 percent / DIEA / dimethylformamide / 4 h / 0 - 20 °C

4: PyBOP; DIEA / dimethylformamide / 4 h / 0 - 20 °C

5: 90 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

6: BOP; DIEA / 4 h / 0 - 20 °C

With lithium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00031-3

Reference yield:

L-cyclohexylalanine (27527-05-5) → Pyrazine-2-carboxylic acid ((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-hydroxy-3-oxo-3-pyrrolidin-1-yl-propylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butyl)-amide (676265-55-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / DIEA / dimethylformamide / 8 h / 0 - 20 °C

2: 95 percent / TFA / CH₂Cl₂

3: 90 percent / DIEA / dimethylformamide / 8 h / 0 - 20 °C

4: 95 percent / TFA / CH₂Cl₂

5: 79 percent / DIEA / dimethylformamide / 4 h / 0 - 20 °C

6: PyBOP; DIEA / dimethylformamide / 4 h / 0 - 20 °C

7: 90 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

8: BOP; DIEA / 4 h / 0 - 20 °C

With lithium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00031-3

Reference yield:

N-(tert-butoxy)carbonyl-L-isoleucine N-hydroxysuccinimide ester (3392-08-3) → Pyrazine-2-carboxylic acid ((S)-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((S)-1-ethyl-2-hydroxy-3-oxo-3-pyrrolidin-1-yl-propylcarbamoyl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-3-methyl-butyl)-amide (676265-55-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / DIEA / dimethylformamide / 8 h / 0 - 20 °C

2: 95 percent / TFA / CH₂Cl₂

3: 90 percent / DIEA / dimethylformamide / 8 h / 0 - 20 °C

4: 95 percent / TFA / CH₂Cl₂

5: 79 percent / DIEA / dimethylformamide / 4 h / 0 - 20 °C

6: PyBOP; DIEA / dimethylformamide / 4 h / 0 - 20 °C

7: 90 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

8: BOP; DIEA / 4 h / 0 - 20 °C

With lithium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00031-3

upstream raw materials:

pyrrolidine

(S)-3-[(S)-3-Cyclohexyl-2-((2S,3S)-3-methyl-2-{(S)-4-methyl-2-[(pyrazine-2-carbonyl)-amino]-pentanoylamino}-pentanoylamino)-propionylamino]-2-hydroxy-pentanoic acid

Boc-Leu-ONSu

L-cyclohexylalanine

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