88820-88-6

Basic information

• Product Name: 4-Pentynoicacid,2-amino-2-methyl-,methylester,(2S)-(9CI)
• Synonyms: 4-Pentynoicacid,2-amino-2-methyl-,methylester,(2S)-(9CI)
• CAS NO: 88820-88-6
• Molecular Formula: C7H11NO2
• Molecular Weight: 0
• Product Categories: GLYCINESCAFFOLD
• Mol File: 88820-88-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Pentynoicacid,2-amino-2-methyl-,methylester,(2S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentynoicacid,2-amino-2-methyl-,methylester,(2S)-(9CI)(88820-88-6)
• EPA Substance Registry System: 4-Pentynoicacid,2-amino-2-methyl-,methylester,(2S)-(9CI)(88820-88-6)

Safety Data

• Hazardous Substances Data: 88820-88-6(Hazardous Substances Data)

Upstream product

• 81136-91-6 (2R,5S)-5-Isopropyl-3,6-dimethoxy-2-methyl-2-prop-2-ynyl-2,5-dihydro-pyrazine 
• 67-56-1 methanol 
• 403519-98-2 (2R)-2-amino-2-methylpent-4-ynoic acid 
• 1422252-96-7 ethyl 2-[(4-methoxyphenyl)amino]-2-methyl-4-pentynoate 

Relevant articles and documents

Synthesis of Structurally Diverse N-Substituted Quaternary-Carbon-Containing Small Molecules from α,α-Disubstituted Propargyl Amino Esters

N-containing quaternary stereocenters represent important motifs in medicinal chemistry. However, due to their inherently sterically hindered nature, they remain underrepresented in small molecule screening collections. As such, the development of synthetic routes to generate small molecules that incorporate this particular feature are highly desirable. Herein, we describe the diversity-oriented synthesis (DOS) of a diverse collection of structurally distinct small molecules featuring this three-dimensional (3D) motif. The subsequent derivatisation and the stereoselective synthesis exemplified the versatility of this strategy for drug discovery and library enrichment. Chemoinformatic analysis revealed the enhanced sp3 character of the target library and demonstrated that it represents an attractive collection of biologically diverse small molecules with high scaffold diversity.

Novel Compounds

The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R is C1-4 alkyl useful in the treatment of diseases and conditions for which antagonism of NK1 receptor is beneficial.

5-[5-[2-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-2-METHYLPROPANOYLMETHYLAMINO]-4-(4-FLUORO-2-METHYLPHENYL)]-2-PYRIDINYL-2-ALKYL-PROLINAMIDE AS NK1 RECEPTOR ANTAGONISTS

The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R is C1-4 alkyl useful in the treatment of diseases and conditions for which antagonism of NK1 receptor is beneficial.

ENANTIOSELECTIVE SYNTHESIS OF NON-PROTEINOGENIC AMINO ACIDS VIA METALLATED BIS-LACTIM ETHERS OF 2,5-DIKETOPIPERAZINES

Bis-lactim ethers 1 of 2,5-diketopiperazines contain a chiral inducing center, an acidic CH-bond and two sites susceptible to hydrolysis.They react with BuLi to give Li compounds of type 4, 15, 29 or 32, which possess a prochiral C atom.They readily add electrophiles (such as alkylating agents or carbonyl compounds) with unusually high diastereoface differentiation.In many cases the d.e-value (d.e. = diastereomeric excess = asymmetric induction) of the adduct exceeds 95percent.On hydrolysis the adducts are cleaved liberating the chiral auxiliary (used to build up the bis-lactim ether 1) and the target molecules, the optically active amino acid methyl esters of type 8, 19, 25 or 36.The two amino acid esters are separable either by fractional distillation or (eventually after further hydrolysis to amino acids) by chromatography.Transition state models are discussed that could explain the exceptionally high asymmetric induction and the predictability of the induced configuration.