(2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

Base Information

• Chemical Name: (2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide
• CAS No.: 401810-35-3
• Molecular Formula: C₂₇H₃₆N₄O₃
• Molecular Weight: 464.608
• Mol file: 401810-35-3.mol

Synonyms:(2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

Chemical Property of (2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

There total 16 articles about (2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-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: 98.0%

(2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-3-carbamoyl-2-({[(fluoren-9-ylmethoxy)carbonylamino]cyclohexy}carbonylamino)propanamide (350038-51-6) → (2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (401810-35-3)

Guidance literature:

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

DOI:10.1021/ol0157609

Reference yield: 93.0%

tert-butyl (1-(((S)-4-amino-1-(((S)-2-(naphthalen-1-ylmethyl)pent-4-en-1-yl)amino)-1,4-dioxobutan-2-yl)carbamoyl)cyclohexyl)carbamate → (2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (401810-35-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1016/j.bmcl.2021.128354

Reference yield:

(2S)-2-amino-N1-[(2S)-2-(naphthylmethyl)-4-pentenyl]butanediamide (401810-36-4) → (2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (401810-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / HOBt; DIPCDI / dimethylformamide / 20 °C

2: piperidine / acetonitrile / 2 h / 20 °C

With piperidine; 1,3-di-tert-butylcarbodiimide; benzotriazol-1-ol; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm0203635

upstream raw materials:

(2S)-N-[(2S)-2-(naphthylmethyl)pent-4-enyl]-3-carbamoyl-2-({[(fluoren-9-ylmethoxy)carbonylamino]cyclohexy}carbonylamino)propanamide

1-[((9H-fluoren-9-yl)methoxy)carbonylamino]cyclohexanecarboxylic acid

(2S)-2-amino-N¹-[(2S)-2-(naphthylmethyl)-4-pentenyl]butanediamide

pent-4-enoic acid

Downstream raw materials:

2-[(9S,13S,17R)-8,11,20-triaza-17-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13-(naphthylmethyl)-7,10,19-trioxospiro[5.14]icos-15-en-9-yl]acetamide

2-[(9S,13S,18S)-8,11,21-triaza-18-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13-(naphthylmethyl)-7,10,20-trioxospiro[5.15]henicos-15-en-9-yl]acetamide

N-{[N-((1S)-1-{N-[(2S)-2-(naphthylmethyl)pent-4-enyl]carbamoyl}-2-carbamoylethyl)carbamoyl]cyclohexyl}-(2S,3R)-2-amino-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)pent-4-enamide

tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate