(2S,5S)-5-[[(2S)-1-[[(2S)-2-acetamido-3-phenylpropanoyl]amino]-1-oxohexan-2-yl]amino]-N-butyl-6-cyclohexyl-4-hydroxy-2-propan-2-ylhexanamide

Base Information

• Chemical Name: (2S,5S)-5-[[(2S)-1-[[(2S)-2-acetamido-3-phenylpropanoyl]amino]-1-oxohexan-2-yl]amino]-N-butyl-6-cyclohexyl-4-hydroxy-2-propan-2-ylhexanamide
• CAS No.: 138571-29-6
• Molecular Formula: C₃₆H₆₀N₄O₅
• Molecular Weight: 628.896
• DSSTox Substance ID: DTXSID80930154
• Mol file: 138571-29-6.mol

Synonyms:APCMN;N-acetylphenylalanyl-N-(4-((butylamino)carbonyl)-1-(cyclohexylmethyl)-2-hydroxy-5-methylhexyl)norleucinamide

Chemical Property of (2S,5S)-5-[[(2S)-1-[[(2S)-2-acetamido-3-phenylpropanoyl]amino]-1-oxohexan-2-yl]amino]-N-butyl-6-cyclohexyl-4-hydroxy-2-propan-2-ylhexanamide

Chemical Property:

• Vapor Pressure: 4.5E-30mmHg at 25°C
• Boiling Point: 841.5°Cat760mmHg
• Flash Point: 462.7°C
• PSA: 136.63000
• Density: 1.063g/cm³
• LogP: 6.36710
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 20
• Exact Mass: 628.45637103
• Heavy Atom Count: 45
• Complexity: 885

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C(=O)NC(=O)C(CC1=CC=CC=C1)NC(=O)C)NC(CC2CCCCC2)C(CC(C(C)C)C(=O)NCCCC)O
• Isomeric SMILES: CCCC[C@@H](C(=O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C)N[C@@H](CC2CCCCC2)C(C[C@@H](C(C)C)C(=O)NCCCC)O

Technology Process of (2S,5S)-5-[[(2S)-1-[[(2S)-2-acetamido-3-phenylpropanoyl]amino]-1-oxohexan-2-yl]amino]-N-butyl-6-cyclohexyl-4-hydroxy-2-propan-2-ylhexanamide

There total 7 articles about (2S,5S)-5-[[(2S)-1-[[(2S)-2-acetamido-3-phenylpropanoyl]amino]-1-oxohexan-2-yl]amino]-N-butyl-6-cyclohexyl-4-hydroxy-2-propan-2-ylhexanamide 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: 50.0%

acetic anhydride (108-24-7) + L-phenylalanyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-L-norleucinamide (138571-27-4) → N-acetyl-L-phenylalanyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-L-norleucinamide (138571-29-6)

Guidance literature:

In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jm00083a006

Reference yield:

(2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid n-butyl amide (105852-64-0) → N-acetyl-L-phenylalanyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-L-norleucinamide (138571-29-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 34 percent / N-hydroxybenzotriazole, DCC / CH₂Cl₂ / Ambient temperature

2: 68 percent / hydrazine hydrate / ethanol / 3 h / Heating

3: 50 percent / CH₂Cl₂ / 1 h / Ambient temperature

With benzotriazol-1-ol; hydrazine hydrate; dicyclohexyl-carbodiimide; In ethanol; dichloromethane;

DOI:10.1021/jm00083a006

Reference yield:

L-2-aminohexanoic acid-methyl ester hydrochloride (3844-54-0) → N-acetyl-L-phenylalanyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-L-norleucinamide (138571-29-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) triethylamine, N-hydroxybenzotriazole, 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / 1.) CH₂Cl₂, 2.) CH₂Cl₂, RT, overnight

2: 60 percent / aq. HCl / acetone / 5 h / Heating

3: 34 percent / N-hydroxybenzotriazole, DCC / CH₂Cl₂ / Ambient temperature

4: 68 percent / hydrazine hydrate / ethanol / 3 h / Heating

5: 50 percent / CH₂Cl₂ / 1 h / Ambient temperature

With hydrogenchloride; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; In ethanol; dichloromethane; acetone;

DOI:10.1021/jm00083a006

upstream raw materials:

acetic anhydride

L-phenylalanyl-N-<4(S)-<(butylamino)carbonyl>-1(S)-(cyclohexylmethyl)-2(S)-hydroxy-5-methylhexyl>-L-norleucinamide

(2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid n-butyl amide

L-2-aminohexanoic acid-methyl ester hydrochloride

Refernces