101055-56-5

Basic information

• Product Name: (2S)-(+)-1-BENZOYL-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE
• Synonyms: (2S)-(+)-1-BENZOYL-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE;(S)-1-BENZOYL-2-TERT-BUTYL-3-METHYL- 4-IMIDAZOLIDINONE;(S)-(+)-1-BENZOYL-2-TERT-BUTYL-3-METHYL- 4-IMIDAZOLIDINONE, 99% (99% EE/GLC);4-Imidazolidinone, 1-benzoyl-2-(1,1-dimethylethyl)-3-methyl-, (2S)-;(2S)-(+)-1-BENZOYL-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE 99+%;(S)-1-Benzoyl-2-(tert-butyl)-3-MethyliMidazolidin-4-one;(2S)-1-benzoyl-2-tert-butyl-3-methylimidazolidin-4-one
• CAS NO: 101055-56-5
• Molecular Formula: C₁₅H₂₀N₂O₂
• Molecular Weight: 260.33
• Mol File: 101055-56-5.mol

Chemical Properties

• Melting Point: 145-147 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2S)-(+)-1-BENZOYL-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(+)-1-BENZOYL-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(101055-56-5)
• EPA Substance Registry System: (2S)-(+)-1-BENZOYL-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(101055-56-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 101055-56-5(Hazardous Substances Data)

Usage

Purification Methods

Recrystallise these chiral imidazolinones from boiling EtOH (solubility is 1.43g/mL) or better by dissolving in CH2Cl2 and adding pentane, filtering and drying for at least 12hours at 60o/0.1mm and sublime them at 135o/0.01mm. They have also been purified by flash column chromatography through Merck silica gel at 0.04-0.063mm and using Et2O/pet ether/MeOH (60:35:5) as eluent. They are then recrystallised from EtOH/pet ether. [IR, NMR: Seebach et al. Helv Chim Acta 70 237 1987, Fitzi & Seebach Angew Chem, Int Ed Engl 25 345 1986.] The racemate is purified in a similar manner and has m 104-105o [NMR: Seebach et al. Helv Chim Acta 68 949 1985].

Upstream product

• 98-88-4 benzoyl chloride 
• 101143-56-0 (2R)-2-(tert-butyl)-3-methylimidazolidin-4-one 
• 119838-37-8 (R)-2-t-butyl-3-methyl-4-imidazolidinone-(R)-mandelate 
• 137348-69-7 (S)-1-benzoyl-2-tert-butyl-3(H)-1,3-imidazolidin-4-one 
• 77-78-1 dimethyl sulfate 
• 137348-66-4 (S,S)-1-benzoyl-2-tert-butyl-3-(α-phenylethyl)-1,3-imidazolidin-4-one 
• 137348-64-2 2-N-(2,2'-dimethylpropyliden)amino-N'-(α-phenylethyl)acetamide 
• 611-71-2 (R)-Mandelic Acid 
• 630-19-3 pivalaldehyde 
• 101055-55-4 (+/-)-2-(tert-butyl)-3-methylimidazolidin-4-one 
• 97443-89-5 (2S,5S)-1-benzoyl-2-(tert-butyl)-3-methyl-5-(3'-thiabutyl)imidazolidin-4-one 
• 109918-56-1 (2S,5S)-1-benzoyl-2-(tert-butyl)-3-methyl-5-vinylimidazolidin-4-one 

Downstream Products

• 119838-35-6 (2S,5S)-1-benzoyl-2-t-butyl-5-(2-hydroxyethyl)-3-methyl-4-imidazolidinone 
• 111610-34-5 (2R,5S,1'R)-5-(benzoyloxy(4-pyridyl)methyl)-2-(tert-butyl)-3-methylimidazolidin-4-one 
• 111623-04-2 (2S,5S,1'R)-1-benzoyl-2-(tert-butyl)-5-((2-furanyl)hydroxymethyl)-3-methylimidazolidin-4-one 
• 111610-29-8 (2R,5S,1'R)-5-(1'-benzoyloxy-2',2',2'-trifluoroethyl)-2-(tert-butyl)-3-methylimidazolidin-4-one 
• 137965-31-2 (2S,5S,1'R)-1-Benzoyl-5-<1'-hydroxy-2'-(4''-nitrophenyl)ethyl>-2-tert-butyl-3-methylimidazolidin-4-one 
• 157457-71-1 (2S,3R)-2-Amino-3-hydroxy-4-(4-chlorophenyl)butanoic acid 
• 157543-53-8 (2S,3R)-2-Amino-3-hydroxy-4-phenylbutanoic acid 
• 111610-31-2 (2R,5S,αR)-4-(α-benzoyloxybenzyl)-2-(tert-butyl)-1-methylimidazolidin-4-one 
• 157401-59-7 (2S,5S)-5-Allyl-1-benzoyl-2-tert-butyl-3-methyl-imidazolidin-4-one 
• 194666-37-0 Benzoic acid (S)-1-((2R,4S)-2-tert-butyl-1-methyl-5-oxo-imidazolidin-4-yl)-2-fluoro-ethyl ester 
• 111610-38-9 (2R,5S,1'R,2'R)-5-((E)-1'-benzoyloxy-2'-methyl-4'-hexenyl)-2-(tert-butyl)-1,3-dimethylimidazolidin-4-one 
• 111646-96-9 (1R,2R,2'S,4E)-1-(N₁,N₂-dimethylglycinamide-2'-yl)-2-methyl-4-hexenyl benzoate 
• 6254-48-4 (2S,3R)-3-phenylserine 

Relevant articles and documents

Alternative Method for the Resolution of 1-Benzoyl-2-tert-butyl-3-methyl-1,3-imidazolidin-4-one

The title heterocycles, which are useful chiral precursors for the asymmetric synthesis of α-amino acids, an be prepared in enantiomerically pure form via the separation of diastereomeric derivatives incorporating (S)-α-methyl-benzylamine.

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.

Addition of Chiral Glycine, Methionine, and Vinylglycine enolate Derivatives to Aldehydes and Ketones in the Preparation of Enantiomerically Pure α-Amino-β-hydroxy Acids

Chiral enolates of imidazolidinones and oxazolidinones from the title amino acids react with carbonyl compounds to afford the corresponding alcohols in excellent yields (see Scheme 5).Furthermore, the addition to aldehydes proceeds with high diastereoselectivity to give, after acid hydrolysis, threo-α-amino-β-hydroxy acids of high enantiomeric purity.Some of the threo-α-amino-β-hydroxy acids prepared in this work are the proteinogenic (S)-threonine (26), the naturally occuring (S)-3-phenylserine (28), and (S)-3-hydroxyleucine (27) as well as the unnatural (S)-4,4,4-rtifluorothreonine (30) and (S)-3-(4-pyridyl)serine (31).The N-methylamide of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoic acid (32), the uniqe amino acid in the immunosuppressive cyclosporine, was prepared by the new method.This report presents also information suggesting that both steric and stereoelectronic effects are responsible for the good stereoselectivities observed.

Methionine as Precursor for the Enantioselective Synthesis of α-Branched Vinylglycines and of Other Amino Acids

Methionine is converted by previously published methods into the diastereoisomerically pure 3-thiabutyl-substituted oxazolidinone (7) and imidazolidinones 5 and 6.An X-ray crystal structure determination of cis-3-benzoyl-2-(tert-butyl)-4-(3-thiabutyl)oxaz