(2S)-N-[(1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methylhexyl]-2-[(S)-1-morpholinocarbonyl-2-phenylethylamino]hexanamide

Base Information

• Chemical Name: (2S)-N-[(1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methylhexyl]-2-[(S)-1-morpholinocarbonyl-2-phenylethylamino]hexanamide
• CAS No.: 130316-76-6
• Molecular Formula: C₃₃H₅₅N₃O₅
• Molecular Weight: 573.817
• DSSTox Substance ID: DTXSID401101118
• Nikkaji Number: J474.623F
• Pharos Ligand ID: J2C2KANK37ZA
• ChEMBL ID: CHEMBL46022
• Mol file: 130316-76-6.mol

Synonyms:CHEMBL46022;DTXSID401101118;2-(1-Benzyl-2-morpholin-4-yl-2-oxo-ethylamino)-hexanoic acid (1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-amide;BDBM50006142;(2S)-N-[(1S,2R,3S)-1-(Cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl]-2-[[(1S)-2-(4-morpholinyl)-2-oxo-1-(phenylmethyl)ethyl]amino]hexanamide;(2S)-N-[(1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methylhexyl]-2-[(S)-1-morpholinocarbonyl-2-phenylethylamino]hexanamide;130316-76-6

Chemical Property of (2S)-N-[(1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methylhexyl]-2-[(S)-1-morpholinocarbonyl-2-phenylethylamino]hexanamide

Chemical Property:

• XLogP3: 5.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 16
• Exact Mass: 573.41417186
• Heavy Atom Count: 41
• Complexity: 747

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC(C(=O)NC(CC1CCCCC1)C(C(CC(C)C)O)O)NC(CC2=CC=CC=C2)C(=O)N3CCOCC3
• Isomeric SMILES: CCCC[C@@H](C(=O)N[C@@H](CC1CCCCC1)[C@H]([C@H](CC(C)C)O)O)N[C@@H](CC2=CC=CC=C2)C(=O)N3CCOCC3

Technology Process of (2S)-N-[(1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methylhexyl]-2-[(S)-1-morpholinocarbonyl-2-phenylethylamino]hexanamide

There total 23 articles about (2S)-N-[(1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methylhexyl]-2-[(S)-1-morpholinocarbonyl-2-phenylethylamino]hexanamide 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:

L-phenylalanine tert-butyl ester hydrochloride (15100-75-1,75898-47-4) → (2S,4S)-3-aza-4-(morpholinocarbonyl)-2-butyl-5-phenylpentanamide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (130316-76-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 9 percent / NaCNBH₃, NaOAc / ethanol / 18 h / Ambient temperature

2: 4 M HCl / dioxane / 16 h

3: 1.) 1-hydroxybenzotriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

4: H₂ / Pd/C

5: 1.) 1-hydroxybenztriazole hydrate (HOBT), N-methylmorpholine (NMM), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

With 4-methyl-morpholine; hydrogenchloride; hydrogen; sodium acetate; sodium cyanoborohydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In 1,4-dioxane; ethanol;

DOI:10.1021/jm00088a006

Reference yield:

2-Oxo-hexanoic acid benzyl ester (130317-29-2) → (2S,4S)-3-aza-4-(morpholinocarbonyl)-2-butyl-5-phenylpentanamide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (130316-76-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 9 percent / NaCNBH₃, NaOAc / ethanol / 18 h / Ambient temperature

2: 4 M HCl / dioxane / 16 h

3: 1.) 1-hydroxybenzotriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

4: H₂ / Pd/C

5: 1.) 1-hydroxybenztriazole hydrate (HOBT), N-methylmorpholine (NMM), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

With 4-methyl-morpholine; hydrogenchloride; hydrogen; sodium acetate; sodium cyanoborohydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In 1,4-dioxane; ethanol;

DOI:10.1021/jm00088a006

Reference yield:

(2S,4S)-benzyl 3-aza-4-(tert-butoxycarbonyl)-2-butyl-5-phenylpentanoate (130316-59-5) → (2S,4S)-3-aza-4-(morpholinocarbonyl)-2-butyl-5-phenylpentanamide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (130316-76-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 4 M HCl / dioxane / 16 h

2: 1.) 1-hydroxybenzotriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

3: H₂ / Pd/C

4: 1.) 1-hydroxybenztriazole hydrate (HOBT), N-methylmorpholine (NMM), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -23 deg C, 2.) DMF, from -23 deg C to RT, 18 h

With 4-methyl-morpholine; hydrogenchloride; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In 1,4-dioxane;

DOI:10.1021/jm00088a006

upstream raw materials:

morpholine

(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(S)-2-[((S)-1-Benzyl-2-morpholin-4-yl-2-oxo-ethyl)-tert-butoxycarbonyl-amino]-hexanoic acid