2292-53-7

Usage

Class

Organic compounds

Subclass

Phenylacetamides

Usage

Intermediate in the synthesis of various pharmaceuticals and biologically active compounds

Molecular Structure

Contains two hydroxyl groups attached to the phenylacetamide backbone

Versatility

Valuable building block for the production of drugs and other organic molecules

Potential Applications

Medicinal chemistry and drug discovery

Industries

Pharmaceutical and chemical

Unique Features

DHPA's molecular structure and the presence of two hydroxyl groups make it a versatile compound for various applications.

InChI:InChI=1/C8H9NO3/c10-7(8(11)9-12)6-4-2-1-3-5-6/h1-5,7,10,12H,(H,9,11)

Upstream product

• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 4358-87-6 (RS)-methyl mandelate 
• 124097-40-1 (2S)-(+)-2-hydroxy-2-phenylacetohydroxamic acid 

Downstream Products

• 100-52-7 benzaldehyde 
• 7568-93-6 2-Amino-1-phenylethanol 
• 87651-26-1 O-Mandeloylbenzaldoxim 
• 121129-35-9 2-Mandeloyl-3,6-dihydro-3,6-methano-2H-1,2-oxazine 
• 121129-39-3 2-Mandeloyl-3,6-dihydro-3,6-ethano-2H-1,2-oxazine 
• 76440-90-9 3-Hydroxy-5-phenyloxazolidine-2,4-dione 
• 121129-43-9 Acetic acid (S)-2-(1S,4R)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-en-3-yl-2-oxo-1-phenyl-ethyl ester 
• 121129-43-9 Acetic acid (S)-2-(1R,4S)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-en-3-yl-2-oxo-1-phenyl-ethyl ester 
• 115501-45-6 Sr(II) (mandelohydroxamic acid)2*(H₂O) 
• 115501-53-6 Pb(II) (mandelohydroxamic acid)2 

Relevant academic research and scientific papers

Preparation of hydroxamic acids from esters in solution and on the solid phase

The present invention provides a novel method for the formation of hydroxamic acids comprising reacting under suitable conditions an ester with hydroxylamine in the presence of cyanide anion.

Improved solution- and solid-phase preparation of hydroxamic acids from esters

The addition of small amounts of solid KCN to solution and solid-phase esters in THF/MeOH/50% aqueous NH2OH increases the efficiency of their transformation to the corresponding hydroxamic acids.

Controlled racemization and asymmetric transformation of α-substituted carboxylic acids in the melt

The racemization and asymmetric transformation of a series of α- substituted carboxylic acids, viz. mandelic acid, hydratropic acid, ibuprofen and naproxen, were studied. Several racemization methods for mandelic acid were studied and it was found that base-catalyzed racemization in aprotic polar solvents was the most efficient method. Moreover, a fast and mild base- catalyzed racemization reaction in the melt was developed. DBN turned out to be a very efficient racemizing base for the substrates studied. Combination of the base-catalyzed racemization in the melt with known resolution processes resulted in crystallization-induced asymmetric transformations. Treating racemic ibuprofen or hydratropic acid with 1.5-2.5 equivalents of enantiopure α-methylbenzylamine and a catalytic amount of DBN resulted in the isolation of enantiomerically enriched ibuprofen or hydratropic acid with ees of up to 75% and almost quantitative yields.

ASYMMETRIC INDUCTION IN THE DIELS-ALDER REACTIONS OF α-HYDROXYACYLNITROSO COMPOUNDS

Transient, chiral α-hydroxyacylnitroso compounds (2), able to form intramolecular hydrogen bonds, react stereoselectively with cyclopentadiene and cyclohexa-1,3-diene; the cycloadduct (6) of the latter diene and the nitroso derivative of (S)-mandelic acid