N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

Base Information

• Chemical Name: N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide
• CAS No.: 666259-67-2
• Molecular Formula: C₂₆H₃₇N₅O₃
• Molecular Weight: 467.611
• Mol file: 666259-67-2.mol

Synonyms:N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

Chemical Property of N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

There total 12 articles about N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide 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: 86.0%

N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-3-carbamoyl-2-({[(fluoren-9-ylmethoxy)carbonylamino]cyclohexyl}carbonylamino)propanamide (852715-08-3) → N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2)

Guidance literature:

With piperidine; In acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1021/jm030440b

Reference yield:

2-{(2S)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}-2-hydrocyclopenta[1,2-a]benzene-1,3-dione (666259-64-9) → N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 84 percent / NH₂NH₂ / ethanol; H₂O / 3 h / Heating

2.1: 1-hydroxybenzotriazole; diisopropylcarbodiimide / dimethylformamide / 0.17 h / 20 °C

2.2: dimethylformamide / 12 h / 20 °C

3.1: 491 mg / aq. HCl / acetonitrile / 12 h / 20 °C

4.1: 83 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 12 h / 20 °C

5.1: 86 percent / piperidine / acetonitrile / 1.5 h / 20 °C

With piperidine; hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; hydrazine; diisopropyl-carbodiimide; In ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm030440b

Reference yield:

(2S)-2-[(5-methylindol-1-yl)methyl]pent-4-en-1-ol (666259-63-8) → N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 12 h / 20 °C

2.1: 84 percent / NH₂NH₂ / ethanol; H₂O / 3 h / Heating

3.1: 1-hydroxybenzotriazole; diisopropylcarbodiimide / dimethylformamide / 0.17 h / 20 °C

3.2: dimethylformamide / 12 h / 20 °C

4.1: 491 mg / aq. HCl / acetonitrile / 12 h / 20 °C

5.1: 83 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 12 h / 20 °C

6.1: 86 percent / piperidine / acetonitrile / 1.5 h / 20 °C

With piperidine; hydrogenchloride; di-isopropyl azodicarboxylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; hydrazine; diisopropyl-carbodiimide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Mitsunobu reaction;

DOI:10.1021/jm030440b

upstream raw materials:

N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-3-carbamoyl-2-({[(fluoren-9-ylmethoxy)carbonylamino]cyclohexyl}carbonylamino)propanamide

3-(5-methylindol-1-yl)propanoic acid

(2S)-2-[(5-methylindol-1-yl)methyl]pent-4-en-1-ol

(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enylamine

Downstream raw materials:

tert-butyl 3-[N-({N-[1-(N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}carbamoyl)(1S)-2-carbamoylethyl]carbamoyl}cyclohexyl)carbamoyl](3S,4S)-4-(4-{[bis(tert-butoxy)carbonyl]methyl}phenyl)hept-6-enoate

tert-butyl 2-[4-(1-{1-[N-({N-[1-(N-{(2R)-2-[(5-methylindolyl)methyl]-4-enyl}carbamoyl)-(1S)-2-carbamoylethyl]carbamoyl}cyclohexyl)carbamoyl]-(1S)-2-[(tert-butyl)oxycarbonyl]ethyl}-(1S)-prop-2-enyl)phenyl]propane-1,3-dioate

tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-nitrophenyl]hex-5-enoate

tert-butyl 3-[N-({N-1-(N-{(2R)-2-[(5-methylindolyl)methyl]pent-4-enyl}-(1S)-2-carbamoylethyl)carbamoyl}cyclohexyl)carbamoyl]-(3S,4S)-4-[4-(tert-butoxy)phenyl]hex-5-enoate