65484-49-3

Basic information

• Product Name: (4S)-4-(3'',4''-Dimethoxybenzyl)-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on
• CAS NO: 65484-49-3
• Molecular Weight: 352.433
• Mol File: 65484-49-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4S)-4-(3'',4''-Dimethoxybenzyl)-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-(3'',4''-Dimethoxybenzyl)-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on(65484-49-3)
• EPA Substance Registry System: (4S)-4-(3'',4''-Dimethoxybenzyl)-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on(65484-49-3)

Safety Data

• Hazardous Substances Data: 65484-49-3(Hazardous Substances Data)

Upstream product

• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 65484-40-4 2-Isocyan-N-<(S)-1'-phenylethyl>propionsaeureamid 
• 65484-49-3 5-(3,4-Dimethoxy-benzyl)-5-methyl-3-((S)-1-phenyl-ethyl)-3,5-dihydro-imidazol-4-one 
• 65484-48-2 (4S)-4-Benzyl-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 65484-43-7 4-Methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 67981-42-4 Alanin-<(S)-1'-phenylethyl>amid 
• 65484-40-4 2-Isocyano-N-(1-phenyl-ethyl)-propionamide 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 

Downstream Products

• 65484-24-4 (R)-5-Benzyl-5-methyl-3-((S)-1-phenyl-ethyl)-3,5-dihydro-imidazol-4-one 
• 65484-43-7 4-Methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 78274-27-8 Pivalinsaeure-<4-methyl-1-(1'-phenylethyl)-5-imidazolyl>ester 
• 78284-00-1 Benzoesaeure-<4-methyl-1-(1'-phenylethyl)-5-imidazolyl>ester 
• 65484-50-6 (4S)-4-Methyl-4-(1''-naphthylmethyl)-1-<1'-phenylethyl>-2-imidazolin-5-on 
• 65484-51-7 (4S)-4-Methyl-4-(2''-naphthylmethyl)-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 65484-54-0 (4S)-4-(3''-Benzothienylmethyl)-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 65484-37-9 (4S)-4-(2''-Brom-3''-benzofuranylmethyl)-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 65484-40-4 2-Isocyan-N-<(S)-1'-phenylethyl>propionsaeureamid 
• 65484-48-2 (4S)-4-Benzyl-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 65484-52-8 (4R)-4-Methyl-1-<(S)-1'-phenylethyl>-4-(2''-thienylmethyl)-2-imidazolin-5-on 
• 65484-52-8 (4S)-4-Methyl-1-<(S)-1'-phenylethyl>-4-(2''-thienylmethyl)-2-imidazolin-5-on 
• 81014-80-4 (4R)-4-(3'',4''-Dimethoxybenzyl)-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 5934-66-7 DL-N-Acetyl-α-methyl-β-<3,4-dimethoxy-phenyl>-alanin 

Relevant articles and documents

Asymmetric Syntheses via Heterocyclic Intermediates, IV. - Asymmetric Synthesis of α-Methylphenylalanine and its Analogues by Alkylation of 1-chiral Substituted 4-Methyl-2-imidazoline-5-one

Treatment of 2-isocyano-N-propionamide (3a) with butyllithium or potassium tert-butoxide (-70 deg C, tetrahydrofuran) initially causes metalation and subsequent (at ca. -20 deg C) cyclization to give the anionized 4-methyl-1--2-imidazolin-5-one (8).This reacts with benzyl or heterobenzyl halides to yield (4S)-4-benzyl- or (4S)-4-heterobenzyl-4-methyl-1--2-imidazolin-5-ones 9 with an asymmetric induction (d.e. = diastereomeric excess) >>95percent.Hydrolysis of 9 gives α-methylphenylalanine or its analogues of type 11 (nearly optically pure) which have been characterized as their N-acetyl derivatives 12.More over, (S)-1-phenylethylamine (2a), the chiral auxiliary compound, is recovered. - With non-benzylic alkyl halides d.e. is much lower (i.e. with allyl bromide 17percent, with cyclohexylmethyl iodide 35percent). - A model concept for the asymmetric induction which also explains the extremely high asymmetric induction with benzyl halides is proposed. - Methods for the synthesis of 2- unsubstituted 4-alkyl-2-imidazolin-5-ones (type 9a, 15-17) and 2-substituted 4-alkyl-2-imidazolin-5-ones (type 18-20) are described. - The X-ray analysis of 4-benzyl-4-methyl-1-(1'-phenylethyl)-2-imidazolin-5-one (9b) shows a) the "phenyl inside conformation" (folded conformation) for the C-4-benzyl group and b) C-1' fixed in such a way that the hydrogen atom of the phenylethyl group lies in the heterocyclic plane, pointing towards the carbonyl oxygen.