367966-41-4

Basic information

• Product Name: BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER
• Synonyms: BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER;N-T-BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER;N-t-BOC-trans-4-Hydroxy-5-oxo-L-proline methyl ester
• CAS NO: 367966-41-4
• Molecular Formula: C11H17NO6
• Molecular Weight: 259.26
• Mol File: 367966-41-4.mol

Chemical Properties

• Melting Point: 90-92 °C
• Boiling Point: 412.6°C at 760 mmHg
• Flash Point: 203.4°C
• Appearance: /
• Density: 1.309g/cm³
• Vapor Pressure: 1.56E-08mmHg at 25°C
• Refractive Index: 1.512
• PKA: 12.51±0.40(Predicted)
• CAS DataBase Reference: BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER(367966-41-4)
• EPA Substance Registry System: BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER(367966-41-4)

Safety Data

• Hazardous Substances Data: 367966-41-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly nucleosides. Its unique structure allows for the creation of novel molecules with potential therapeutic applications.
BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER is used as a building block for the synthesis of 3-Guaninyland 3-Adeninyl-5-hydroxymethyl-2-pyrrolidinone Nucleosides. These nucleosides have potential applications in the development of new drugs for the treatment of various diseases, including cancer and viral infections. The synthesis of these nucleosides relies on the unique reactivity and structural features of BOC-4-HYDROXY-5-OXO-L-PROLINE METHYL ESTER, making it a valuable component in the pharmaceutical industry.

InChI:InChI=1/C11H17NO6/c1-11(2,3)18-10(16)12-6(9(15)17-4)5-7(13)8(12)14/h6-7,13H,5H2,1-4H3/t6-,7+/m0/s1

Upstream product

• 267420-70-2 1-(tert-butyl) 2-methyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 114676-91-4 1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 226225-42-9 (2S,4R)-N-tert-butyloxycarbonyl-4-[(tert-butyldiphenylsilyl)oxy]pyrrolidine-2-carboxylic acid methyl ester 
• 367966-67-4 1-(tert-butyl) 2-methyl (2S,4S)-4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate 

Downstream Products

• 716361-98-7 (2S,4R)-4-hydroxy-5-oxopyrrolidine-2-carboxylic acid 
• 367966-46-9 (2S,4R)-4-(4-Chloro-naphthalen-1-yloxy)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Relevant articles and documents

POLYMYXIN ANALOGS USEFUL AS ANTIBIOTIC POTENTIATORS

The disclosure provides compounds of the formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt of either of the foregoing. The variables A, R1, and R2 are defined in the disclosure. The disclosure further includes pharmaceutical compositions comprising a compound of formula I together with at least one pharmaceutically acceptable carrier. The disclosure also includes a method of sensitizing bacteria to an antibacterial agent, comprising administering to a patient infected with the bacteria, simultaneously or sequentially, a therapeutically effective amount of the antibacterial agent and a compound of formula (I).

Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

A convenient and high yield method to prepare 4-hydroxypyroglutamic acids

RuO2/NaIO4 oxidation of N-Boc-4-silyloxy and 4-acetoxy proline methyl esters under ethyl acetate/water biphase condition gave N-Boc-4-silyloxy and 4-acetoxy pyroglutamic acid derivatives in high yields. Desilylation with TBAF afforded both cis- and trans-N-Boc-methyl-4-hydroxy pyroglutamates.