(S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic acid

Base Information

• Chemical Name: (S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic acid
• CAS No.: 1539320-81-4
• Molecular Formula: C₂₈H₄₂N₄O₇
• Molecular Weight: 546.664

Synonyms:(S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic acid

Chemical Property of (S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic acid

Chemical Property:

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Technology Process of (S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic acid

There total 7 articles about (S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic 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:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → (S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic acid (1539320-81-4)

Guidance literature:

Multi-step reaction with 6 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h

2: trifluoroacetic acid / dichloromethane / 2 h

3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 °C

4: trifluoroacetic acid / dichloromethane / 2 h

5: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h

6: lithium hydroxide dihydrate / tetrahydrofuran; water

With dmap; lithium hydroxide dihydrate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c3ob42016g

Reference yield:

(S)-Leu-OMe (2666-93-5) → (S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic acid (1539320-81-4)

Guidance literature:

Multi-step reaction with 6 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h

2: trifluoroacetic acid / dichloromethane / 2 h

3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 °C

4: trifluoroacetic acid / dichloromethane / 2 h

5: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h

6: lithium hydroxide dihydrate / tetrahydrofuran; water

With dmap; lithium hydroxide dihydrate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c3ob42016g

Reference yield:

tert-butyl (2S)-2-{[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]carbamoyl}pyrrolidine-1-carboxylate (15136-16-0) → (S)-2-((S)-1-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methyl pentanoic acid (1539320-81-4)

Guidance literature:

Multi-step reaction with 5 steps

1: trifluoroacetic acid / dichloromethane / 2 h

2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 °C

3: trifluoroacetic acid / dichloromethane / 2 h

4: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h

5: lithium hydroxide dihydrate / tetrahydrofuran; water

With lithium hydroxide dihydrate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c3ob42016g

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

(S)-Leu-OMe

tert-butyl (2S)-2-{[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]carbamoyl}pyrrolidine-1-carboxylate

L-proline-L-leucine methyl ester

Downstream raw materials:

tert-butyl ((R)-1-((2-((S)-2-(((S)-1-((4-bromophenyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carbonyl)-phenyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate

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