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Methyl 2-amino-2-phenylacetate hydrochloride, also known as Phenylglycine Methyl Ester Hydrochloride, is a substituted glycine derivative characterized by the presence of a phenyl group and an amino group in its molecular structure. methyl 2-amino-2-phenylacetate hydrochloride exhibits unique chemical properties that make it a versatile building block in the pharmaceutical industry.

15028-40-7

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15028-40-7 Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 2-amino-2-phenylacetate hydrochloride is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of a wide range of therapeutic agents, making it a valuable component in the development of new drugs.
Used in Enzymatic Synthesis of Penicillin:
In the field of antibiotics, methyl 2-amino-2-phenylacetate hydrochloride plays a crucial role as a compound involved in the enzymatic synthesis of D-(-)-α-Aminobenzyl penicillin by Penicillin Acylase. This application highlights its importance in the production of life-saving medications.
Used in the Chemical Industry:
Methyl 2-amino-2-phenylacetate hydrochloride is also utilized in the chemical industry for the production of various specialty chemicals and materials. Its unique properties make it a suitable candidate for the development of new compounds with specific applications in areas such as coatings, adhesives, and polymers.

Check Digit Verification of cas no

The CAS Registry Mumber 15028-40-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,0,2 and 8 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 15028-40:
(7*1)+(6*5)+(5*0)+(4*2)+(3*8)+(2*4)+(1*0)=77
77 % 10 = 7
So 15028-40-7 is a valid CAS Registry Number.

15028-40-7Relevant articles and documents

Synthesis of 3-Hydroxymethyl Isoindolinones via Cobalt-Catalyzed C(sp2)-H Carbonylation of Phenylglycinol Derivatives

Lukasevics, Lukass,Cizikovs, Aleksandrs,Grigorjeva, Liene

supporting information, p. 2720 - 2723 (2020/03/30)

An efficient method for the synthesis of 3-hydroxymethyl isoindolinones via cobalt-catalyzed C(sp2)-H carbonylation of phenylglycinol derivatives using picolinamide as a traceless directing group is demonstrated. The reaction proceeds in the presence of a commercially available cobalt(II) tetramethylheptanedionate catalyst and employs DIAD as a "CO" surrogate. This synthetic route offers a broad substrate scope, excellent regioselectivity, and full preservation of the original stereochemistry. Besides, the developed method provides a pathway for accessing valuable enantiopure 3-substituted isoindolinone derivatives.

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.

supporting information, p. 4703 - 4708 (2019/06/27)

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

Synthesis of unnatural α-amino acid derivatives: Via selective o -C-H functionalization

Zeng, Wanting,Nukeyeva, Moldir,Wang, Qiumei,Jiang, Chao

supporting information, p. 598 - 608 (2018/02/09)

Pd-Catalyzed o-C-H functionalization of α-phenylglycine, 4-hydroxyphenylglycine and phenylalanine using picolinamide as a directing group is reported. We have developed different protocols for the arylation, alkylation, alkynylation, halogenation, alkoxylation, and acyloxylation of these amino acids. The reactions exhibit high selectivity, broad substrate scope, and compatibility with different functional groups in moderate to high yields. They provide a rapid and efficient access to a variety of phenyl based amino acid derivatives which can be further modified and have broad spectrum of applications in medicinal chemistry.

Treatment of proliferative disorders with a chemiluminescent agent

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Page/Page column 31; 32, (2016/10/31)

Methods employing chemiluminescent agents as therapeutically active agents in the treatment of proliferative disorders are disclosed. The chemiluminiscent agents are used in the disclosed method without a therapeutically effective amount of a photosensitizer. Novel chemiluminescent agents having the general formula: are also disclosed, wherein X, Y, Z, R3 and R5-R9 are as defined herein.

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Wang, Tianli,Yu, Zhaoyuan,Hoon, Ding Long,Phee, Claire Yan,Lan, Yu,Lu, Yixin

supporting information, p. 265 - 271 (2016/01/25)

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Access to α-Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide

Guo, Chun-Xiao,Zhang, Wen-Zhen,Zhou, Hui,Zhang, Ning,Lu, Xiao-Bing

, p. 17156 - 17159 (2016/11/23)

A straightforward and transition-metal-free approach for the efficient synthesis of α-arylglycine derivatives from aromatic imines and carbon dioxide was enabled by an umpolung carboxylation reaction. Various substituted diphenylmethimines underwent the carboxylation smoothly with carbon dioxide in the presence of potassium tert-butoxide and 18-crown-6 to give the corresponding carboxylated products in good to high yields. Besides the enhancement of the solubility of potassium tert-butoxide in THF, 18-crown-6 also plays key roles in suppressing the reverse protonation or 1, 3-proton shift isomerization as well as by stabilizing the carboxylated intermediate.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

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Paragraph 0235, (2014/05/20)

Disclosed herein are new heterocyclic compounds of Formula IIa: and compositions thereof, and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Triple role of phenylselenonyl group enabled a one-pot synthesis of 1,3-oxazinan-2-ones from α-isocyanoacetates, phenyl vinyl selenones, and water

Buyck, Thomas,Wang, Qian,Zhu, Jieping

supporting information, p. 11524 - 11528 (2014/10/15)

Reaction of α-substituted α-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

Catalytic enantioselective Michael addition of α-aryl-α- isocyanoacetates to vinyl selenone: Synthesis of α,α-disubstituted α-amino acids and (+)- and (-)-trigonoliimine A

Buyck, Thomas,Wang, Qian,Zhu, Jieping

supporting information, p. 12714 - 12718 (2013/12/04)

Be like Mike: The title reaction in the presence of the catalyst 1 afforded Michael adducts in excellent yields and enantioselectivities. The adducts were readily converted into α,α′-disubstituted α-amino acids. The enantioselective total synthesis of bot

Iron-catalyzed oxidative C - H/C - H cross-coupling: An efficient route to α-quaternary α-amino acid derivatives

Li, Kaizhi,Tan, Guangying,Huang, Jingsheng,Song, Feijie,You, Jingsong

supporting information, p. 12942 - 12945 (2014/01/06)

Fully loaded: A coordinating activation strategy has been developed to furnish α-quaternary α-amino acids through the iron(III)-catalyzed oxidative functionalization of α-C(sp3) - H bonds of α-tertiary α-amino acid esters. The reaction exhibits a broad substrate scope for both α-amino acids and nucleophiles (Nu) as well as good functional-group tolerance (see scheme, DTBP=di-tert-butyl peroxide, DCE=1,2-dichloroethane). Copyright

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