2799-15-7

Usage

Uses

Used in Pharmaceutical Industry:
D-a-Methyl DOPA is used as an antihypertensive agent for the treatment of hypertension (high blood pressure). It works by stimulating the production of prolactin, which in turn leads to the conversion of norepinephrine to epinephrine, resulting in a decrease in blood pressure. This makes it a valuable compound in the management of hypertension and related cardiovascular conditions.
Additionally, D-a-Methyl DOPA is used as an impurity in the synthesis of Methyldopa, which is an essential component in the production of antihypertensive medications. The rapid formation of methyl ester when reacting with methanol highlights its potential for further chemical modifications and applications in the pharmaceutical industry.

Synthetic route

(2R,5R)-1-benzoyl-2-(tert-butyl)-5-(3',4'-dimethoxybenzyl)-3,5-dimethylimidazolidin-4-one (98262-53-4) → L-3-(3,4-dihydroxyphenyl)-2-methylalanine (2799-15-7)

Conditions	Yield
With hydrogenchloride at 175 - 185℃; for 4h; Yield given;

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) → L-3-(3,4-dihydroxyphenyl)-2-methylalanine (2799-15-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / -78 - 0 °C 2: aq. 6N HCl / 4 h / 175 - 185 °C View Scheme

phthalic anhydride (85-44-9) + L-3-(3,4-dihydroxyphenyl)-2-methylalanine (2799-15-7) → C28H28N2O10

Conditions	Yield
In neat (no solvent)

Upstream product

• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 98262-53-4 (2R,5R)-1-benzoyl-2-(tert-butyl)-5-(3',4'-dimethoxybenzyl)-3,5-dimethylimidazolidin-4-one 

Relevant academic research and scientific papers

α-Alkylation of Amino Acids without Racemization. Preparation of Either (S)- or (R)-α-Methyldopa from (S)-Alanine

Enantiomerically pure cis- and trans-5-alkyl-1-benzoyl-2-(tert-butyl)-3-methylimidazolidin-4-ones (1, 2, 11, 15, 16) and trans-2-(tert-butyl)-3-methyl-5-phenylimidazolidin-4-one (20), readily available from (S)-alanine, (S)-valine, (S)-methionine, and (R)-phenylglycine are deprotonated to chiral enolates (cf. 3, 4, 12, 21).Diastereoselective alkylation of these enolates to 5,5-dialkyl- or 5-alkyl-5-arylimidazolidinones (5, 6, 9, 10, 13a-d, 17, 18, 22) and hydrolysis give α-alkyl-α-amino acids such as (R)- and (S)-α-methyldopa (7 and 8a, resp.), (S)-α-methylvaline (14), and (R)-α-methyl-methionine (19).The configuration of the products is proved by chemical correlation and by NOE 1H-NMR measurements (see 23, 24).In the overall process, a simple, enantiomerically pure α-amino acid can be α-alkylated with retention or with inversion of configuration through pivalaldehyde acetal derivatives.Since no chiral auxiliary is required, the process is coined 'self-reproduction of a center of chirality'.The method is compared with other α-alkylations of amino acids occuring without racemization.The importance of enantiomerically pure, α-branched α-amino acids as synthetic intermediates and for the preparation of biologically active compounds is discussed.