25705-52-6

Usage

Uses

Used in Pharmaceutical Industry:
(R)-phenylglycine hydrochloride is used as a chiral auxiliary for the asymmetric synthesis of various pharmaceuticals and agrochemicals. It aids in the production of enantiomerically pure compounds, which are vital for the development of many modern drugs.
Used in Chiral Drug Production:
(R)-phenylglycine hydrochloride is used as a key component in the production of chiral drugs. Its chiral nature ensures the synthesis of drugs with specific stereochemistry, which is crucial for their therapeutic effects and safety.
Used in Research and Development:
(R)-phenylglycine hydrochloride is utilized in research and development within the pharmaceutical and agrochemical industries. It serves as a valuable tool for the synthesis and study of chiral compounds, contributing to the advancement of new drug discoveries and agrochemical innovations.

InChI:InChI=1/C8H9NO2.ClH/c10-8(11)6-9-7-4-2-1-3-5-7;/h1-5,9H,6H2,(H,10,11);1H

Upstream product

• 29129-67-7 (S)-2-azido-2-phenylacetic acid 
• 151671-03-3 tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate 
• 127383-03-3 (3R,5R,6S)-4-(tert-Butoxycarbonyl)-2,3,5,6-tetrahydro-3,5,6-triphenyl-1,4-oxazin-2-one 
• 393588-13-1 (2R,αR)-2-phenyl-2-(N-benzyl-N-α-methylbenzylamino)ethanoic acid 
• 226388-27-8 (R)-α-(N,N-dibenzylamino)-α-phenylacetic acid 
• 117681-86-4 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate 
• 65253-04-5 (-)-8-phenylmenthol 
• 116911-14-9 (2S,3S)-3-azido-3-phenyl-propane-1,2-diol 
• 100-52-7 benzaldehyde 
• 226388-23-4 (αR,3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl α-(N,N-dibenzylamino)-α-phenylacetate 
• 393588-04-0 (2R,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)-3-phenylpropanol 
• 393588-07-3 (2R,αR)-2-phenyl-2-(N-benzyl-N-α-methylbenzylamino)ethanal 
• 14990-09-1 tert-butyl cinnamate 
• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 

Downstream Products

• 79795-33-8 C₁₅H₁₅N₂O₃P 
• 79795-33-8 C₁₅H₁₅N₂O₃P 
• 33125-05-2 Boc-D-Phg-OH 
• 15686-71-2 cefalexin 
• 1007880-00-3 (R)-2-(3-cyclopentylureido)-2-phenylacetic acid 
• 54193-09-8 HPGly 
• 1007879-96-0 (R)-tert-butyl 2-(3-cyclopentylureido)-2-phenylacetate 
• 6489-76-5 D-(-)-N-carbamoyl phenyl glycine 
• 26553-34-4 N-trichloroethoxycarbonyl-D-phenylglycine 

Relevant academic research and scientific papers

Axially chiral dicarboxylic acid-catalyzed asymmetric imino aza-enamine reaction/oxidation as a Strecker reaction surrogate

Axially chiral dicarboxylic acid-catalyzed highly enantioselective imino aza-enamine reaction was elaborated into a surrogate of the asymmetric Strecker reaction building on the fact that the N,N-dialkylhydrazone moiety can be easily converted to the cyanide moiety by treatment with peracid.

A practical synthesis of optically active arylglycines via catalytic asymmetric Strecker reaction

A practical procedure for catalytic asymmetric synthesis of optically active arylglycine derivatives via optically active α-aminonitriles has been developed. The N-benzhydryl α-arylaminonitrile intermediates were prepared in excellent yield (89-99%) and enantiomeric purity (96 to >98% ee) by enantioselective cyanation of aldimines with TMSCN/iPrOH in the presence of 2.5 mol % of an easily prepared Ti/chiral amino alcohol complex at 0 °C, without requiring slow addition of the cyanating agent. The easily racemized α-aminonitrile intermediates were efficiently hydrolyzed by an aqueous HCl/TFA mixture to give the arylglycine derivatives in good yield (60-92%) and moderate to excellent enantiomeric purity (85-98% ee).

Asymmetric allylboration of α,β-enals as a surrogate for the enantioselective synthesis of allylic amines and α-amino acids

(Chemical Equation Presented) Optically pure allylic amines have been synthesized from α,β-unsaturated aldehydes via allylboration with (-)-B-allyldiisopinocampheylborane, followed by Overman rearrangement. By incorporating crotyl and alkoxyallylboration, functionalization at δ-position was readily accomplished. By applying this methodology, the synthesis of several chiral α-amino acids has been achieved.

Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

An efficient protocol for the transformation of homochiral α-hydroxy-β-amino esters to their α-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino 1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-α-methylbenzyl protected α-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the α-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides α-amino acids in 94-98% e.e.

Synthesis of chiral α-amino acids

A novel method for the synthesis of chiral α-amino acids has been developed where the acid functionality was constructed by oxidizing a hydroxymethyl group introduced by Evans' method in the α-position of an appropriate acid substrate and the amino part came from the amide of the original carboxyl group following a modified Hofmann rearrangement reaction.

Asymmetric synthesis of α-amino carbonyls (aldehydes, ketones and acids) using lithium (R)-N-benzyl-N-α-methylbenzylamide

The diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated esters and subsequent enolate hydroxylation, followed by reduction and oxidative cleavage provides a facile route to N,N-protected α-amino aldehydes and ketones. Further manipulation furnishes α-amino acids in high enantiomeric excess.

(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-amino acids

rac-α-Amino acids (rac-1a-d) were formally deracemized by a four-step reaction sequence: (a) protection of the amino function as the phthalimido derivative; (b) acyl chloride formation; (c) diastereoselective reaction with the chiral auxiliaries (R)- or (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2- pyrrolidinone, (R)- or (S)-3; and (d) acid hydrolysis to deprotect both the ester and phthalimido functions. Diastereoselectivities of the intermediate esters 4 were good (82-96% d.e.), except for the case of 4b (41% d.e.), the precursor of valine. The main diastereoisomer of esters 4 was (αR,3S)- or (αS,3R)-, except for 4d: in this case, working at -78°C, the (αR,3R)- diastereoisomer was the main product, which epimerizes easily at the α- position when at room temperature. Acid hydrolysis of esters 4 directly gave the deprotected α-amino acids, with little or no epimerization at the α- position of the α-amino acid and complete recovery of the chiral auxiliary. Only (αR,3R)-4d on acid hydrolysis partially epimerized at the α-position. Moreover, some α-amino acids and their N,N-dibenzyl derivatives were obtained by dynamic kinetic resolution of diastereoisomeric mixtures of α- bromo esters 5 derived from the chiral auxiliaries (R)- or (S)-3 during reaction with dibenzylamine.

Synthesis of Optically Active Arylglycines by Photolysis of Optically Active (β-Hydroxyamino) Carbene-Chromium(0) Complexes

Photolysis of chromium complexes having the optically active amino alcohol (1R,2S)-(-)- or (1S,2R)-(+)-2-amino-1,2-diphenylethanol as the amino group produced aryl-substituted oxazinones in good yield with reasonable diastereoselectivity.Facile separation of diastereoisomers followed by mild reductive cleavage produced several arylglycines, having either electron-donating or withdrawing groups on the aromatic ring, in good overall yield and with excellent enantiomeric excess.

Asymmetric synthesis of arylglycines

The asymmetric synthesis of several arylglycines are reported. The methodology deployed involves either cuprate or Friedel - Crafts couplings to chiral bromoglycinates. The % ee's range from 82 to 94%. Both an oxidative and reductive protocol are employed to unmask the oxazinone chiral auxilliary providing the free α-amino acids.