N-(4-Amino-1-benzyl-3-hydroxy-5-phenyl-pentyl)-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide 5-oxopyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: N-(4-Amino-1-benzyl-3-hydroxy-5-phenyl-pentyl)-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide 5-oxopyrrolidine-2-carboxylic acid
• CAS No.: 192726-06-0
• Molecular Formula: C27H38N4O3^.C5H7NO3
• Molecular Weight: 595.73
• Mol file: 192726-06-0.mol

Synonyms:[1S-[1R*(R*),3R*,4R*]]-N-[4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide,5-Oxo-L-proline salt;[1S-[1R*(R*),3R*,4R*]]-N-[4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide;N-(4-Amino-1-benzyl-3-hydroxy-5-phenyl-pentyl)-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide 5-oxopyrrolidine-2-carboxylic acid (THP);

Chemical Property of N-(4-Amino-1-benzyl-3-hydroxy-5-phenyl-pentyl)-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide 5-oxopyrrolidine-2-carboxylic acid

Chemical Property:

• PSA: 174.09000
• LogP: 3.51110

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)butanamidecompdwith(S)-5-oxopyrrolidine-2-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(4-Amino-1-benzyl-3-hydroxy-5-phenyl-pentyl)-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide 5-oxopyrrolidine-2-carboxylic acid

There total 12 articles about N-(4-Amino-1-benzyl-3-hydroxy-5-phenyl-pentyl)-3-methyl-2-(2-oxo-tetrahydro-pyrimidin-1-yl)-butyramide 5-oxopyrrolidine-2-carboxylic acid 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: 74.0%

[1S]-N-[4-amino-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-R-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide + L-Pyroglutamic acid (98-79-3) → (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt (192726-06-0)

Guidance literature:

In 1,4-dioxane; at 20 - 50 ℃; for 1h; Inert atmosphere;

DOI:10.1021/op990202j

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-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt (192726-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / Inert atmosphere

2: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / Inert atmosphere

3: 5%-palladium/activated carbon; ammonium formate / methanol / 50 °C / Inert atmosphere

4: 1,4-dioxane / 1 h / 20 - 50 °C / Inert atmosphere

With 1H-imidazole; thionyl chloride; 5%-palladium/activated carbon; ammonium formate; In tetrahydrofuran; 1,4-dioxane; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/op990202j

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) + L-Pyroglutamic acid (98-79-3) → (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt (192726-06-0)

Guidance literature:

(2S,3S,5S)-2-N,N-dibenzylamino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane; With ammonium formate; 5% Pd(II)/C(eggshell); In methanol; at 50 - 55 ℃; for 2h;

L-Pyroglutamic acid; In ethyl acetate; N,N-dimethyl-formamide; at 50 - 55 ℃; for 2h; Product distribution / selectivity;

upstream raw materials:

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

L-Pyroglutamic acid

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

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

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF SUBSTANTIALLY PURE (2S,3S,5S)-5-AMINO-2-N,N-DIBENZYLAMINO-3-HYDROXY-1,6-DIPHENYLHEXANE". Page/Page column 4. . Retrieved 2010/12/29.
• 2、 -. "Processes and intermediates for preparing retroviral protease inhibitors". Example 2. . Retrieved 2008/06/13.