(S) 3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRYL CHLORIDE

Base Information

• Chemical Name: (S) 3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRYL CHLORIDE
• CAS No.: 192800-77-4
• Molecular Formula: C₉H₁₅ClN₂O₂
• Molecular Weight: 218.683
• Mol file: 192800-77-4.mol

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

Chemical Property of (S) 3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRYL CHLORIDE

Chemical Property:

• Solubility.: Acetone, Chloroform

Purity/Quality:

97% ^*data from raw suppliers

(S)-Tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S) 3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRYL CHLORIDE

There total 4 articles about (S) 3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRYL CHLORIDE 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: 100.0%

(S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid (192725-50-1) → 2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride (192800-77-4)

Guidance literature:

With thionyl chloride; In tetrahydrofuran; at 4 - 20 ℃; for 5.5h; Inert atmosphere;

DOI:10.1021/op990202j

Reference yield:

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → 2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride (192800-77-4)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium chloride; lithium hydroxide; aluminum oxide / water / 5 h / -20 - -10 °C / pH 9.5 - 10.2 / Inert atmosphere

2: sodium hydroxide / tetrahydrofuran / 2 h / 2 - 10 °C / Inert atmosphere

3: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

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

With aluminum oxide; thionyl chloride; potassium tert-butylate; lithium chloride; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; water; 1: |Schotten-Baumann Reaction;

DOI:10.1021/op990202j

Reference yield:

(2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid (126147-70-4) → 2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride (192800-77-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / tetrahydrofuran / 2 h / 2 - 10 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

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

With thionyl chloride; potassium tert-butylate; sodium hydroxide; In tetrahydrofuran;

DOI:10.1021/op990202j

upstream raw materials:

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

L-valine

(2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid

Downstream raw materials:

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

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

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

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、 -. "PROCESSES FOR THE PREPARATION OF LOPINAVIR AND ITS INTERMEDIATE - (S)-TETRAHYDRO-ALPHA-(1-METHYLETHYL)-2-OXO-1(2H)-PYRIMIDINEACETIC ACID". Page/Page column 10. . Retrieved 2010/11/24.