62965-56-4

Basic information

• Product Name: (S)-(-)-4-tert-Butyloxazolidine-2,5-dione
• Synonyms: L-TERT-LEUCINE NCA;(S)-4-TERT-BUTYLOXAZOLIDINE-2,5-DIONE;L-tert-Leucine N-carboxyanhydride
• CAS NO: 62965-56-4
• Molecular Formula: C₇H₁₁NO₃
• Molecular Weight: 157.17
• EINECS: -0
• Product Categories: Leucine [Leu, L]
• Mol File: 62965-56-4.mol

Chemical Properties

• Melting Point: 132°C
• Appearance: /
• Density: 1.164g/cm³
• Refractive Index: 1.464
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 4664497
• CAS DataBase Reference: (S)-(-)-4-tert-Butyloxazolidine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-4-tert-Butyloxazolidine-2,5-dione(62965-56-4)
• EPA Substance Registry System: (S)-(-)-4-tert-Butyloxazolidine-2,5-dione(62965-56-4)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 62965-56-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-(-)-4-tert-Butyloxazolidine-2,5-dione is used as a key intermediate for the synthesis of various organic compounds. Its unique structure allows for selective functionalization and modification, making it a versatile building block in the construction of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-(-)-4-tert-Butyloxazolidine-2,5-dione is utilized as a starting material or intermediate in the development of new drugs. Its reactivity and structural features enable the creation of novel bioactive molecules with potential therapeutic applications.
Used in Agrochemicals:
(S)-(-)-4-tert-Butyloxazolidine-2,5-dione is also employed in the agrochemical sector as a precursor for the synthesis of various agrochemical products, such as pesticides and herbicides. Its unique properties allow for the development of new compounds with improved efficacy and selectivity.
Used in Dye Industry:
In the dye industry, (S)-(-)-4-tert-Butyloxazolidine-2,5-dione is used as a raw material for the production of various dyes and pigments. Its structural features contribute to the development of dyes with enhanced color properties and stability.

InChI:InChI=1/C7H11NO3/c1-7(2,3)4-5(9)11-6(10)8-4/h4H,1-3H3,(H,8,10)

Upstream product

• 70874-05-4 Z-D-Tle 
• 75-44-5 phosgene 
• 20859-02-3 L-tert-Leucine 

Downstream Products

• 62965-57-5 (S)-(+)-2-amino-3,3-dimethylbutanamide 
• 13007-90-4 bis(triphenylphosphine)nickel⁽⁰⁾ dicarbonyl 
• 89226-12-0 L-tert-leucine methylamide 
• 67151-54-6 N-acetyl-L-tert-leucine N'-methylamide 
• 63009-42-7 (R)-2-((S)-2-Amino-3,3-dimethyl-butyrylamino)-3-phenyl-propionic acid methyl ester 
• 84907-94-8 (2R,5S)-2-Benzyl-5-tert-butyl-3,6-dimethoxy-2,5-dihydro-pyrazine 
• 65050-07-9 Cyclo(L-tert-Leu-Gly) 
• 63038-26-6 (S)-2-amino-3,3-dimethyl-butyric acid methyl ester 

Relevant articles and documents

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.