119906-46-6

Basic information

• Product Name: (R)-1-Z-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE
• Synonyms: (R)-(+)-1-(BENZYLOXYCARBONYL)-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE;(R)-1-Z-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE;(R)-(+)-1-(BENZYLOXYCARBONYL)-2-T-BUTYL&;(R)-Benzyl 2-(tert-butyl)-3-Methyl-4-oxoiMidazolidine-1-carboxylate;(R)-2-t-butyl-1-carbobenzyloxy-3-methyl-4-imidazolidinone;(R)-1-Z-2-tert-butyl-3-methyl-4-imidazolidinone≥ 98% (HPLC)
• CAS NO: 119906-46-6
• Molecular Formula: C₁₆H₂₂N₂O₃
• Molecular Weight: 290.36
• Product Categories: Peptide Synthesis;Precursors for Amino Acid Synthesis;Specialty Synthesis
• Mol File: 119906-46-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 84-86 °C(lit.)
• Boiling Point: 435.9°C at 760 mmHg
• Flash Point: 217.4°C
• Appearance: /
• Density: 1.152g/cm³
• Vapor Pressure: 8.45E-08mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-1-Z-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Z-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(119906-46-6)
• EPA Substance Registry System: (R)-1-Z-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(119906-46-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 119906-46-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

(R)-1-Z-2-tert-butyl-3-methyl-4-imidazolidinone is a chiral glycine derivative used for the synthesis of amino acids.

InChI:InChI=1/C16H22N2O3/c1-16(2,3)14-17(4)13(19)10-18(14)15(20)21-11-12-8-6-5-7-9-12/h5-9,14H,10-11H2,1-4H3/t14-/m1/s1

Upstream product

• 101055-55-4 (+/-)-2-(tert-butyl)-3-methylimidazolidin-4-one 
• 17199-29-0 (S)-Mandelic acid 
• 501-53-1 benzyl chloroformate 
• 119838-36-7 (R)-2-tert-butyl-3-methyl-4-oxoimidazolidinium (R)-mandelate 

Downstream Products

• 123053-51-0 3-benzyl-3'-(tert-butyl) (2R,2'S,4R,4'S)-2,2'-di(tert-butyl)-1,1'-dimethyl-5,5'-dioxo-4,4'-(1,4-butanediyl)-bis(imidazolidine)-3,3'-dicarboxylate 

Relevant articles and documents

RESOLUTION AND USE IN α-AMINO ACID SYNTHESIS OF IMIDAZOLIDINONE GLYCINE DERIVATIVES

The imidazolidinones (rac.-1 and rac.-2) obtained from pivalaldehyde and glycine amides are resolved efficiently by crystallization of diastereomeric ammonium salts with chiral acids (mandelates and a gulonate respectively).The free bases are acylated under Schotten-Baumann conditions to give enantiomerically pure 1-Bz-, 1-BOC-, 1-Z- or 1-formyl-2-t-butyl-3-methyl- or -3-benzyl-4-imidazolidinones.Diastereoselective alkylation of the 3-methyl derivatives (BMI) with a variety of electrophiles (LDA/THF -70 to +25 degC) gives trans-disubstituted imidazolidinones exclusively (3-22).Some of these are hydrolyzed by a procedure employing excess acidic ion exchange resin to give enantiomerically pure (R)- or (S)-amino acids.The procedure is compared with other methods of generating chiral glycine enolates.