(2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N¹-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide

Base Information

• Chemical Name: (2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N¹-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide
• CAS No.: 861640-68-8
• Molecular Formula: C₂₇H₃₆N₄O₄
• Molecular Weight: 480.607

Synonyms:(2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N¹-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide

Chemical Property of (2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N¹-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N¹-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide

There total 12 articles about (2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N¹-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide 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: 90.0%

(1-{(S)-2-Carbamoyl-1-[(S)-2-(5-hydroxy-naphthalen-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (861640-72-4) → (2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N1-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide (861640-68-8)

Guidance literature:

With piperidine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2005.04.028

Reference yield:

(4S)-3-[3-(5-hydroxy-1-naphthalenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2-oxazolidinone (861640-60-0) → (2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N1-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide (861640-68-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 49 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 24 h / 20 °C

2.1: 98 percent / H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

3.1: lithium hexamethyldisilylamide / tetrahydrofuran / 1 h / -78 °C

3.2: tetrahydrofuran / -78 °C

4.1: 86 percent / LiAlH₄ / tetrahydrofuran / -78 °C

5.1: 69 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 15 h / 20 °C

6.1: 87 percent / hydrazine / ethanol; H₂O / 3 h / Heating

7.1: 97 percent / diisopropylcarbodidiimide; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 20 °C

8.1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

9.1: 92 percent / diisopropylcarbodiimide; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 20 °C

10.1: 90 percent / piperidine / acetonitrile / 2 h / 20 °C

With piperidine; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; hydrogen; benzotriazol-1-ol; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; hydrazine; diisopropyl-carbodiimide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 5.1: Mitsunobu reaction;

DOI:10.1016/j.bmc.2005.04.028

Reference yield:

(4S)-3-[3-(5-(2-(trimethylsilyl)ethyl)oxy-1-naphthalenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2-oxazolidinone (861640-61-1) → (2S)-2-[[(1-aminocyclohexyl)carbonyl]amino]-N1-[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]butanediamide (861640-68-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 98 percent / H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

2.1: lithium hexamethyldisilylamide / tetrahydrofuran / 1 h / -78 °C

2.2: tetrahydrofuran / -78 °C

3.1: 86 percent / LiAlH₄ / tetrahydrofuran / -78 °C

4.1: 69 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 15 h / 20 °C

5.1: 87 percent / hydrazine / ethanol; H₂O / 3 h / Heating

6.1: 97 percent / diisopropylcarbodidiimide; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 20 °C

7.1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

8.1: 92 percent / diisopropylcarbodiimide; 1-hydroxybenzotriazole / dimethylformamide / 12 h / 20 °C

9.1: 90 percent / piperidine / acetonitrile / 2 h / 20 °C

With piperidine; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; hydrogen; benzotriazol-1-ol; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; hydrazine; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 4.1: Mitsunobu reaction;

DOI:10.1016/j.bmc.2005.04.028

upstream raw materials:

(1-{(S)-2-Carbamoyl-1-[(S)-2-(5-hydroxy-naphthalen-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

(2S)-(2-propen-1-yl)-3-(5-(2-(trimethylsilyl)ethyl)oxy-1-naphthalenyl)propan-1-ol

(2S)-1-amino-2-(2-propen-1-yl)-3-(5-((2-(trimethylsilyl)ethyl)oxy)-1-naphthalenyl)propane

(4S)-3-[3-(5-hydroxy-1-naphthalenyl)-1-oxo-2-propen-1-yl]-4-phenyl-2-oxazolidinone

Downstream raw materials:

(βS,γS)-β-[[1-[[(1S)-3-amino-1-[[(2S)-2-(5-hydroxy-1-naphthalenylmethyl)-4-pentenyl]aminocarbonyl]-3-oxopropyl]aminocarbonyl]cyclohexyl]aminocarbonyl]-4-[4-[bis(tert-butoxy)phosphoryl]methyl]-γ-ethenylbenzenebutanoic acid 1,1-dimethylethyl ester

(9S,10S,11E,14S,18S)-18-(2-amino-2-oxoethyl)-10-[[4-[bis(1,1-dimethylethoxy)phosphoryl]methyl]phenyl]-14-(1-(5-hydroxy)naphthalenylmethyl)-8,17,20-trioxo-7,16,19-triazaspiro[5.14]eicos-11-en-9-acetic acid 1,1-dimethylethyl ester

C₆₇H₉₆N₇O₁₃PS

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