478698-32-7

Usage

Uses

Used in Pharmaceutical Research:
(2S)-1,2-PYRROLIDINEDICARBOXYLIC ACID,4,4-DIFLUORO-3,3-DIMETHYL-,1-(1,1-DIMETHYLETHYL)ESTER is used as a building block in the synthesis of various bioactive molecules and pharmaceutical intermediates. Its unique chemical structure and properties make it a valuable component in the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (2S)-1,2-PYRROLIDINEDICARBOXYLIC ACID,4,4-DIFLUORO-3,3-DIMETHYL-,1-(1,1-DIMETHYLETHYL)ESTER serves as a key intermediate for the preparation of a wide range of chemical compounds. Its versatility and reactivity contribute to its utility in various synthetic pathways and reactions.

InChI:InChI=1/C12H19F2NO4/c1-10(2,3)19-9(18)15-6-12(13,14)11(4,5)7(15)8(16)17/h7H,6H2,1-5H3,(H,16,17)/t7-/m1/s1

Upstream product

• 854375-33-0 N-tert-butoxycarbonyl-4,4-difluoro-3,3-dimethylproline methyl ester 
• 478698-30-5 3,3-dimethyl-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 848444-88-2 C₁₃H₂₁NO₅ 
• 478698-31-6 (S)-4,4-difluoro-3,3-dimethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Relevant academic research and scientific papers

Process research and development and scale-up of a 4,4-difluoro-3,3- dimethylproline derivative

The multikilogram production of the proline derivative 1, a key intermediate of a HIV protease inhibitor, required the design of a synthetic route able to be safely, effectively, and easily scaled up. Synthesis of the proline skeleton began with construction of racemic glycine derivative 4, via an ester enolate Claisen rearrangement of Boc-glycine 3-methyl-but-2-enyl ester (3) in the absence of a Lewis acid. After a classical resolution of 4 with (S)- phenylglycinol, (S)-4 was transformed into bromo-lactone 6b with NBS. The bromo-lactone was transformed to proline alcohol 8 via a base-promoted rearrangement involving lactone solvolysis. An NMR study suggested that a bicyclic lactone was initially formed, which subsequently opened by the methanol solvent to form 8. The requisite ketone for fluorination was prepared via oxidation of the enantiomerically pure 8, using NaClO and catalytic TEMPO. gem-Difluoro proline 1 was then prepared from the ketone via fluorination with Deoxo-Fluor. During this study it was discovered that SiO2 promoted fluorination by Deoxo-Fluor. This study allowed the production of 7.5 kg of 1 after 10 steps, in 4.5% molar yield and high purity (94-99% HPLC assay).

Efficient enzymatic process for the production of (2S)-4,4-difluoro-3,3- dimethyl-N-Boc-proline, a key intermediate in the synthesis of HIV protease inhibitors

(2S)-4,4-Difluoro-3,3-dimethyl-N-Boc-proline (3) is a key intermediate for the synthesis of HIV protease inhibitors. Here, several approaches for the preparation of enantiopure 3 and its analogues are disclosed. Among these methods, one strategy relies on

METHODS FOR THE PREPARATION OF STEREOISOMERICALLY ENRICHED AMINES

The present invention relates to methods of preparing a stereoisomerically enriched compound of formula (I), wherein R6 is hydrogen, comprising treating a compound of formula (I), wherein R6 is chosen from C1-C10/sub

HIV protease inhibitors, compositions containing the same, their pharmaceutical uses and materials for their synthesis

The present invention concerns processes for preparing compounds of formula (I-H), or a prodrug, pharmaceutically active metabolite, or pharmaceutically active salt or solvate thereof, which are useful as inhibitors of the HIV protease enzyme.