(S)-N-[(2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-YL]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-YL)butanamide

Base Information

• Chemical Name: (S)-N-[(2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-YL]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-YL)butanamide
• CAS No.: 192726-05-9
• Molecular Formula: C27H38N4O3
• Molecular Weight: 466.624
• UNII: 395TR49R7C
• DSSTox Substance ID: DTXSID70172869
• Wikidata: Q27256862
• Mol file: 192726-05-9.mol

Synonyms:192726-05-9;Lopinavir free amine;(S)-N-[(2S,4S,5S)-5-AMINO-4-HYDROXY-1,6-DIPHENYLHEXAN-2-YL]-3-METHYL-2-(2-OXOTETRAHYDROPYRIMIDIN-1(2H)-YL)BUTANAMIDE;(S)-N-((2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-yl)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide;395TR49R7C;N-((2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-yl)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide, (S)-;(2S)-N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide;1(2H)-Pyrimidineacetamide, N-((1S,3S,4S)-4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-alpha-(1-methylethyl)-2-oxo-, (alphaS)-;1(2H)-Pyrimidineacetamide, N-[(1S,3S,4S)-4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-, (alphaS)-;UNII-395TR49R7C;Lopinavir specified impurity A [EP];Lopinavir impurity, lopinavir free amine- [USP];DTXSID70172869;AKOS027447531;LOPINAVIR IMPURITY A [WHO-IP];LOPINAVIR AMINO ALCOHOL [WHO-IP];LOPINAVIR IMPURITY A [EP IMPURITY];DB-290297;LOPINAVIR FREE AMINE [USP IMPURITY];J-012472;Q27256862;(2S)-N-((1S,3S,4S)-1-BENZYL-4-AMINO-3-HYDROXY-5-PHENYLPENTYL)-3-METHYL-2-(2-OXOTETRAHYDROPYRIMIDIN-1(2H)-YL)BUTANAMIDE;(alphaS)-N-[(1S,3S,4S)-4-Amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide;(S)-N-[(2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2;1(2H)-PYRIMIDINEACETAMIDE, N-((1S,3S,4S)-4-AMINO-3-HYDROXY-5-PHENYL-1-(PHENYLMETHYL)PENTYL)TETRAHYDRO-.ALPHA.-(1-METHYLETHYL)-2-OXO-, (.ALPHA.S)-

Chemical Property of (S)-N-[(2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-YL]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-YL)butanamide

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Boiling Point: 762.223 °C at 760 mmHg
• Flash Point: 414.778 °C
• PSA: 114.67000
• Density: 1.154 g/cm³
• LogP: 3.59330
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 466.29439109
• Heavy Atom Count: 34
• Complexity: 631

Purity/Quality:

99% ^*data from raw suppliers

(S)-N-[(2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NC(CC1=CC=CC=C1)CC(C(CC2=CC=CC=C2)N)O)N3CCCNC3=O
• Isomeric SMILES: CC(C)[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C[C@@H]([C@H](CC2=CC=CC=C2)N)O)N3CCCNC3=O

Technology Process of (S)-N-[(2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-YL]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-YL)butanamide

There total 10 articles about (S)-N-[(2S,4S,5S)-5-Amino-4-hydroxy-1,6-diphenylhexan-2-YL]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-YL)butanamide 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:

(S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid (192725-50-1) → (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane (192726-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / tetrahydrofuran / 6 h / 0 - 20 °C

2: imidazole / dimethylformamide; ethyl acetate / 0 - 20 °C

3: HCO₂NH₄ / Pd/C / methanol / 50 °C

With 1H-imidazole; thionyl chloride; ammonium formate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm070284z

Reference yield:

(2S,3S,5S)-2-N,N-dibenzylamino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane (192726-04-8) → (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane (192726-05-9)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; at 50 ℃;

DOI:10.1021/jm070284z

Reference yield:

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane (156732-15-9) → (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane (192726-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide; ethyl acetate / 0 - 20 °C

2: HCO₂NH₄ / Pd/C / methanol / 50 °C

With 1H-imidazole; ammonium formate; palladium on activated charcoal; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm070284z

upstream raw materials:

(2S,3S,5S)-2-N,N-dibenzylamino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane

2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride

(S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid

(2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane

Downstream raw materials:

lopinavir

(2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt

Refernces

• 1、 Reddy, G. S. Kiran Kumar,Ali, Akbar,Nalam, Madhavi N. L.,Anjum, Saima Ghafoor,Cao, Hong,Nathans, Robin S.,Schiffer, Celia A.,Rana, Tariq M.. "Design and synthesis of HIV-1 protease inhibitors incorporating oxazolidinones as P2/P2′ ligands in pseudosymmetric dipeptide isosteres". . p. 4316 - 4328. Retrieved 2008/02/12.
• 2、 -. "Retroviral protease inhibiting compounds". Page 65. . Retrieved 2010/01/31.