(S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester

Base Information

• Chemical Name: (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester
• CAS No.: 187396-10-7
• Molecular Formula: C₄₁H₅₄N₆O₇
• Molecular Weight: 742.916
• Mol file: 187396-10-7.mol

Synonyms:(S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester

Chemical Property of (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester

There total 10 articles about (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester 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: 29.0%

(S)-9-[(R)-2-Amino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-9-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-nonanoic acid; compound with trifluoro-acetic acid → (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester (187396-10-7)

Guidance literature:

With sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 5.5h;

DOI:10.1021/jm9603072

Reference yield:

8-bromooctanoic acid (17696-11-6) → (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester (187396-10-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / H₂SO₄ / diethyl ether

2: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -55 deg C, b) RT, 16 h

3: 10percent aq. citric acid / tetrahydrofuran / 48 h

4: 99 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

5: 55 percent / 0.5 N aq. LiOH / tetrahydrofuran / 4 h / Ambient temperature

6: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

7: 100 percent / H₂ / 10percent Pd/C / methanol / Ambient temperature

8: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

9: 100 percent / anisole / CH₂Cl₂ / 3 h / 0 - 20 °C

10: 29 percent / NaHCO₃, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / dimethylformamide / 5.5 h / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; sulfuric acid; hydrogen; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; methoxybenzene; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9603072

Reference yield:

8-bromo-octanoic acid tert-butyl ester (77383-17-6) → (S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester (187396-10-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -55 deg C, b) RT, 16 h

2: 10percent aq. citric acid / tetrahydrofuran / 48 h

3: 99 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

4: 55 percent / 0.5 N aq. LiOH / tetrahydrofuran / 4 h / Ambient temperature

5: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

6: 100 percent / H₂ / 10percent Pd/C / methanol / Ambient temperature

7: 1.) DIEA, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 2.) DIEA / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, overnight

8: 100 percent / anisole / CH₂Cl₂ / 3 h / 0 - 20 °C

9: 29 percent / NaHCO₃, (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / dimethylformamide / 5.5 h / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; hydrogen; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; methoxybenzene; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9603072

upstream raw materials:

8-bromooctanoic acid

8-bromo-octanoic acid tert-butyl ester

(S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester

(S)-9-Amino-10-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-10-oxo-decanoic acid tert-butyl ester

Downstream raw materials:

(S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid