5688-96-0

Usage

Uses

Used in Organic Synthesis:
(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetyl chloride is used as a chemical intermediate for the synthesis of various organic compounds. Its ability to participate in acylation and nucleophilic substitution reactions allows for the creation of a wide range of new compounds with different functional groups and properties.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetyl chloride is used as a building block for the development of new drugs and biologically active molecules. Its unique structure and reactivity contribute to the design and synthesis of innovative therapeutic agents with potential applications in treating various diseases and medical conditions.

Upstream product

• 2835-06-5 phenylglycin 
• 85-44-9 phthalic anhydride 
• 4695-37-8 N-phthaloyl-DL-2-phenylglycine 

Downstream Products

• 1190731-28-2 N-(4,4-diethoxybutyl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-phenylacetamide 
• 174536-94-8 N-phthalyl (R,R)-phenylglycine pantolactonyl ester 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 

Relevant academic research and scientific papers

Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)-H Direct Fluorination

A coordinating, copper-catalyzed direct α-C(sp3)-H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. A Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled Cu(II) charge transfer complex. The protocol can tolerate a rich variety of α-amino acids, for which the auxiliary group is removed in high yield and substituted for the direct preparation of dipeptide derivatives with detachable, single absolute configurations of the target compounds.

Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene

2-Carbomethoxynorbornene is identified as a more effective transient mediator to promote a Pd(II)-catalyzed meta-C(sp2)-H alkylation of amides with various alkyl iodides as well as arylation with previously incompatible aryl iodides. The use of a tailor-made quinoline ligand is also crucial for this reaction to proceed.

An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: A facile synthesis of Pyrrolo-tetrahydroisoquinolones and Pyrrolo-benzazepinones

The triflic acid-mediated cyclisation of N-arylmethyl- and N-arylethyl-acylpyrrolidinium ions gave moderate to good yields of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones respectively. Electron-donating R substituents enhanced the rate of reaction and gave higher yields than electron-withdrawing substituents. Substituents on the methyl or ethyl chain in general enhanced the reaction, unless sterically encumbered. The equivalent acylpiperidinium ions cyclised much slower and in lower yield.

(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.

Asymmetric synthesis of α-amino acids via diastereoselective addition of (R)-pantolactone to their ketenes

The diastereoselective addition of (R)-pantolactone to various amino ketenes derived from phthalylamino acids is reported. The configuration of the newly-generated asymmetric center is dependent on alkyl or aryl C(x substitution. This method constitutes a novel and convenient way of amino acid deracemization.

A convenient synthesis of optically active phenylglycine

Optically active R phenylglycine methyl ester hydrochloride (ee = 98%) was prepared in 90% yield from racemic phenylglycine. The key step was the base catalysed diastereoselective addition at -78°C of R pantolactone to the N-phthalyl protected phenylglycine ketene.