82659-84-5

Basic information

• Product Name: METHYL (4S,5S)-DIHYDRO-5-METHYL-2-PHENYL-4-OXAZOLECARBOXYLATE
• Synonyms: METHYL (4S,5S)-DIHYDRO-5-METHYL-2-PHENYL-4-OXAZOLECARBOXYLATE;methyl (4S,5S)-dihydro-5-methyl-2-phenyl-4-oxazol;methyl dihydro-5-methyl-2-phenyl-4-oxazolecarboxylate
• CAS NO: 82659-84-5
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Oxazoles
• Mol File: 82659-84-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: 74-76 °C(lit.)
• Boiling Point: 110-115 °C0.01 mm Hg(lit.)
• Flash Point: 156.1°C
• Appearance: /
• Density: 1.1825 (rough estimate)
• Vapor Pressure: 1.42E-06mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• PKA: 2.66±0.70(Predicted)
• CAS DataBase Reference: METHYL (4S,5S)-DIHYDRO-5-METHYL-2-PHENYL-4-OXAZOLECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (4S,5S)-DIHYDRO-5-METHYL-2-PHENYL-4-OXAZOLECARBOXYLATE(82659-84-5)
• EPA Substance Registry System: METHYL (4S,5S)-DIHYDRO-5-METHYL-2-PHENYL-4-OXAZOLECARBOXYLATE(82659-84-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 82659-84-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H13NO3/c1-8-10(12(14)15-2)13-11(16-8)9-6-4-3-5-7-9/h3-8,10H,1-2H3/t8-,10-/m0/s1

Upstream product

• 79893-89-3 N-benzoyl-L-threonine methyl ester 
• 3373-59-9 L-threonine methyl ester 
• 98-88-4 benzoyl chloride 
• 27696-01-1 (2S,3R)-threo-N-benzoyl-threonine 
• 99843-24-0 (4S)-5t-methyl-2-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid 
• 99843-24-0 (+/-)-5t-methyl-2-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid 
• 267653-05-4 N-benzoyl-(2S,3S)-threonine methyl ester 
• 3373-59-9 (2S,3S)-methyl 2-amino-3-hydroxybutanoate 
• 65-85-0 benzoic acid 
• 75-07-0 acetaldehyde 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 7471-86-5 methyl benzimidate 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 60143-52-4 L-threonine methyl ester hydrochloride 

Downstream Products

• 99843-24-0 (4R)-5t-methyl-2-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid 
• 28954-12-3 (2S,3S)-2-amino-3-hydroxybutanoic acid 
• 906324-06-9 N-benzoyl-D_s-threonine 
• 88318-67-6 Lithium; methoxy-[(R)-5-methyl-2-phenyl-oxazol-(4E)-ylidene]-methanolate 
• 114041-55-3 (4R/S,5S)-(4-2H)-4,5-Dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 88318-71-2 (4S,5S)-4-Ethyl-4,5-dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 88318-69-8 (4S,5S)-4,5-Dihydro-4,5-dimethyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 88318-67-6 Lithium; methoxy-[(S)-5-methyl-2-phenyl-oxazol-(4E)-ylidene]-methanolate 
• 93474-57-8 3-hydroxy-2-[(phenylsulfonyl)amino]butanoic acid 

Relevant articles and documents

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.

The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions

A rapid flow synthesis of oxazolines and their oxidation to the corresponding oxazoles is reported. The oxazolines are prepared at room temperature in a stereospecific manner, with inversion of stereochemistry, from β-hydroxy amides using Deoxo-Fluor. The

ETHYNYLBENZENE DERIVATIVES

Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R1, R2, R3, R101, L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.