119838-38-9

Basic information

• Product Name: (S)-(-)-1-(TERT-BUTOXYCARBONYL)-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE
• Synonyms: (S)-(-)-1-BOC-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE 99+%;(S)-tert-Butyl 2-(tert-butyl)-3-Methyl-4-oxoiMidazolidine-1-carboxylate;(S)-1-tert-Butoxycarbonyl-2-tert-butyl-3-Methyl-1,3-iMidazolidin-4-one;(S)-1-Boc-2-tert-butyl-3-MethyliMidazolidin-4-one;(S)-1-Boc-2-tert-butyl-3-methyl-4-imidazolidinone≥ 95% (NMR);S-BOC-BMI;(S)-(-)-1-BOC-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE;(S)-1-BOC-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE
• CAS NO: 119838-38-9
• Molecular Formula: C₁₃H₂₄N₂O₃
• Molecular Weight: 256.34
• Mol File: 119838-38-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 67-69 °C(lit.)
• Boiling Point: 355.3°C at 760 mmHg
• Flash Point: 168.7°C
• Appearance: /
• Density: 1.064g/cm³
• Vapor Pressure: 3.15E-05mmHg at 25°C
• Refractive Index: 1.483
• Storage Temp.: 2-8°C
• PKA: -0.60±0.40(Predicted)
• BRN: 4907144
• CAS DataBase Reference: (S)-(-)-1-(TERT-BUTOXYCARBONYL)-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-(TERT-BUTOXYCARBONYL)-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(119838-38-9)
• EPA Substance Registry System: (S)-(-)-1-(TERT-BUTOXYCARBONYL)-2-TERT-BUTYL-3-METHYL-4-IMIDAZOLIDINONE(119838-38-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 119838-38-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

(2S)-2-(1,1-Dimethylethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylic Acid 1,1-Dimethylethyl Ester is a glycine derivative that is used as starting material for the preparation of open-chain amino acids.

InChI:InChI=1/C13H24N2O3/c1-12(2,3)10-14(7)9(16)8-15(10)11(17)18-13(4,5)6/h10H,8H2,1-7H3/t10-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 119838-37-8 (R)-2-t-butyl-3-methyl-4-imidazolidinone-(R)-mandelate 
• 101055-55-4 (+/-)-2-(tert-butyl)-3-methylimidazolidin-4-one 
• 900503-36-8 (R)-(-)-2-(tert-butyl)-3-methyl-4-imidazolidinone trifluoroacetic acid salt 

Downstream Products

• 137569-27-8 t-butyl (2S,5S,1'R)-2-(t-butyl)-5-<2'-(2,6-di-t-butyl-4-methoxyphenoxycarbonyl)-1'-methylethyl>-3-methyl-4-oxo-1-imidazolidinecarboxylate 
• 137569-28-9 t-butyl (2S,5S,1'R)-2-(t-butyl)-5-<2'-(2,6-di-t-butyl-4-methoxyphenoxycarbonyl)-1'-ethylethyl>-3-methyl-4-oxo-1-imidazolidinecarboxylate 
• 137593-89-6 t-butyl (2S,5S,1'S)-2-(t-butyl)-5-<2'-(2,6-di-t-butyl-4-methoxyphenoxycarbonyl)-1'-(isopropyl)ethyl>-3-methyl-4-oxo-1-imidazolidinecarboxylate 
• 119838-28-7 (2S,5S,1'S)-2-t-butyl-1-t-butyloxycarbonyl-3-methyl-5-(1-methyl-benzyl)-4-imidazolidinone 
• 123052-80-2 (2S,5S)-2-tert-Butyl-5-(3-chloro-benzyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester 
• 123052-79-9 tert-butyl (2S,5S)-2-(tert-butyl)-5-(4-fluorobenzyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate 
• 1027167-32-3 1,1-dimethylethyl (2S)-trans-5-(<1,1'-biphenyl>-3-ylmethyl)-2-(1,1-dimethylethyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate 
• 1093786-40-3 C₂₀H₂₆F₄N₂O₃ 
• 1093786-43-6 C₂₀H₂₆F₄N₂O₃ 
• 1262048-20-3 (2S,5S)-tert-butyl 5-(4-(benzyloxy)-5-(1,3-dithiolan-2-yl)-2-fluorobenzyl)-2-tert-butyl-3-methyl-4-oxoimidazolidine-1-carboxylate 
• 1262048-21-4 (2S,5S)-tert-butyl 2-tert-butyl-5-(2-fluoro-5-(2-methyl-1,3-dithiolan-2-yl)benzyl)-3-methyl-4-oxoimidazolidine-1-carboxylate 
• 1262048-22-5 (2S,5S)-tert-butyl 5-(5-(1,3-dithiolan-2-yl)-2-fluorobenzyl)-2-tert-butyl-3-methyl-4-oxoimidazolidine-1-carboxylate 
• 123052-78-8 tert-butyl (2S,5S)-2-(tert-butyl)-5-(4-deuteriobenzyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate 
• 123052-84-6 tert-butyl (2S,5S)-2-(tert-butyl)-3-methyl-4-oxo-5-(2-thenyl)-1-imidazolidinecarboxylate 

Relevant articles and documents

Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation

Substituting N-methylpyrrole for N-methyindole in secondary-amine-catalysed Friedel-Crafts reactions leads to a curious erosion of enantioselectivity. In extreme cases, this substrate dependence can lead to an inversion in the sense of enantioinduction. Indeed, these closely similar transformations require two structurally distinct catalysts to obtain comparable selectivities. Herein a focussed molecular editing study is disclosed to illuminate the structural features responsible for this disparity, and thus identify lead catalyst structures to further exploit this selectivity reversal. Key to effective catalyst re-engineering was delineating the non-covalent interactions that manifest themselves in conformation. Herein we disclose preliminary validation that intermolecular aromatic (CH-π and cation-π) interactions between the incipient iminium cation and the indole ring system is key to rationalising selectivity reversal. This is absent in the N-methylpyrrole alkylation, thus forming the basis of two competing enantio-induction pathways. A simple L-valine catalyst has been developed that significantly augments this interaction.

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.