394735-22-9

Basic information

• Product Name: (2-CARBAMOYL-1-CYCLOBUTYLMETHYL-2-HYDROXY-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: (2-CARBAMOYL-1-CYCLOBUTYLMETHYL-2-HYDROXY-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER;3-(tert-ButoxycarbonylaMino)-4-cyclobutyl-2-hydroxybutanaMide;N-[3-AMino-1-(cyclobutylMethyl)-2-hydroxy-3-oxopropyl]-carbaMic Acid 1,1-DiMethylethyl Ester;tert-butyl 4-aMino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-ylcarbaMate;tert-Butyl 4-amino-1-cyclobutyl-3,4-dioxobutan-2-ylcarbamate;Carbamic acid, N-[3-amino-1-(cyclobutylmethyl)-2-hydroxy-3-oxopropyl]-, 1,1-dimethylethyl ester
• CAS NO: 394735-22-9
• Molecular Formula: C₁₃H₂₄N₂O₄
• Molecular Weight: 272.343
• Mol File: 394735-22-9.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 468.915°C at 760 mmHg
• Flash Point: 237.391°C
• Appearance: /
• Density: 1.156
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• PKA: 11.82±0.46(Predicted)
• CAS DataBase Reference: (2-CARBAMOYL-1-CYCLOBUTYLMETHYL-2-HYDROXY-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (2-CARBAMOYL-1-CYCLOBUTYLMETHYL-2-HYDROXY-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER(394735-22-9)
• EPA Substance Registry System: (2-CARBAMOYL-1-CYCLOBUTYLMETHYL-2-HYDROXY-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER(394735-22-9)

Safety Data

• Hazardous Substances Data: 394735-22-9(Hazardous Substances Data)

Usage

Description

(2-Carbamoyl-1-cyclobutylmethyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester is a complex organic compound characterized by its white solid appearance. It is a carbamic acid derivative with a cyclobutylmethyl and hydroxy-ethyl group, and a tert-butyl ester functional group. (2-Carbamoyl-1-cyclobutylmethyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester is known for its potential applications in the pharmaceutical industry, particularly in the development of inhibitors for hepatitis C virus (HCV) NS3 serine protease.

Uses

Used in Pharmaceutical Industry:
(2-Carbamoyl-1-cyclobutylmethyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester is used as a key intermediate compound for the synthesis of hepatitis C virus (HCV) NS3 serine protease inhibitors. Its unique structure allows it to interact with the active site of the NS3 protease, thereby inhibiting its function and helping to combat the virus.
Used in Drug Development:
In the field of drug development, (2-Carbamoyl-1-cyclobutylmethyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester serves as a valuable building block for designing and synthesizing novel therapeutic agents. Its chemical properties and reactivity make it a promising candidate for further modification and optimization to enhance its potency, selectivity, and pharmacokinetic properties.
Used in Medicinal Chemistry Research:
(2-Carbamoyl-1-cyclobutylmethyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester is also utilized in medicinal chemistry research to explore its potential as a lead compound for the development of new drugs targeting various diseases. Its structural features can be exploited to design molecules with improved biological activity and reduced side effects.

InChI:InChI=1/C13H24N2O4/c1-13(2,3)19-12(18)15-9(10(16)11(14)17)7-8-5-4-6-8/h8-10,16H,4-7H2,1-3H3,(H2,14,17)(H,15,18)

Upstream product

• 1036931-37-9 3-amino-4-cyclobutyl-2-hydroxybutanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 885280-12-6 ethyl 4-cyclobutyl-3-oxobutanoate 
• 4415-82-1 cyclobutanemethanol 
• 63659-30-3 cyclobutylmethyl methanesulfonate 
• 4426-03-3 cyclobutyl acetonitrile 
• 1433545-85-7 3-[(tert-butoxycarbonyl)amino]-4-cyclobutyl-1-ethoxy-1-oxobut-2-yl 4-methoxybenzoate 
• 1433545-74-4 (2E)-3-amino-4-cyclobutyl-1-ethoxy-1-oxobut-2-en-2-yl 4-methoxybenzoate 
• 1433545-62-0 4-cyclobutyl-1-ethoxy-1,3-dioxobutan-2-yl 4-methoxybenzoate 
• 1433545-53-9 ethyl 2-chloro-4-cyclobutyl-3-oxobutanoate 
• 17247-58-4 (Bromomethyl)cyclobutane 
• 1025799-39-6 2-(benzhydrylidene-amino)-3-cyclobutyl-propionic acid ethyl ester 
• 394735-17-2 ethyl 2-amino-3-cyclobutylpropanoate 
• 394735-21-8 methyl 3-tert-butoxycarbonylamino-4-cyclobutyl-2-hydroxybutyrate 

Downstream Products

• 394735-25-2 {(S)-2-[(1R,2S,5S)-2-(2-Carbamoyl-1-cyclobutylmethyl-2-hydroxy-ethylcarbamoyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hex-3-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 394735-28-5 (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide 
• 394730-60-0 boceprevir 
• 1036931-36-8 3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride 

Relevant articles and documents

A New and convenient synthesis of the boceprevir P1 fragment, β-aminoα-hydroxy amide

A new and convenient synthesis of the P1 fragment of HCV inhibitor, boceprevir is described. This approach efficiently provides P1 fragment of boceprevir using simple and easy handling reagents suitable for scale up. This synthetic route involves the conversion of ester intermediate into novel intermediate, α-chloro ketone via chloroacetate Claisen condensation, followed by further simple conversions to β-amino-α-hydroxy amide, P1 fragment of boceprevir in high yield.

PROCESS AND INTERMEDIATES FOR THE PREPARATION OF 3-AMINO-4-CYCLOBUTYL-2-HYDROXYBUTANAMIDE AND SALTS THEREOF

The present invention relates to synthetic processes useful in the preparation of a compound of Formula (I), and salts thereof. Compounds of Formula (I) and salts thereof have application in the preparation of inhibitors of the hepatitis C virus, such as (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6, 6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide. The present invention also encompasses intermediates useful in the disclosed synthetic processes and the methods of their preparation.

Pharmaceutical formulations and methods of treatment using the same

Pharmaceutical formulations containing at least one compound of Formulae I-XXVI herein and at least one surfactant. Pharmaceutically acceptable carriers and excipients may also be included in the formulations. The formulations of the present invention are suited for use in single unit dosages.