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药物详细合成路线

Name Mexiletine hydrochloride;Mexitil
Chemical Name 1-(2,6-Dimethylphenoxy)-2-propanamine hydrochloride
CAS 5370-01-4
Related CAS 31828-71-4 (free base)
Formula C11H18ClNO
Structure
Formula Weight 215.72521
Stage 上市-1976
Company Boehringer Ingelheim (Originator), Nippon Boehringer Ingelheim (Originator)
Activity/Mechanism Antiarrhythmic Drugs, Antispastic Drugs and Drugs for Muscle Spasms, CARDIOVASCULAR DRUGS, Muscle Spasms, Drugs for, NEUROLOGIC DRUGS, Smooth Muscle Relaxants, Sodium Channel Blockers
Syn. Route 3
Route 1
by hydrogenation of 1-(2,6-dimethylphenoxy)-2-propanoxime (i) with h2 over raney-ni in methanol.
List of intermediates No.
(3ar,9br)-9-methoxy-2-[(1r)-1-phenylethyl]-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole; (3ar,9br)-2-[(1r)-1-phenylethyl]-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrol-9-yl methyl ether (i)
Reference 1:
    koeppe, h.; et al.; za 6903772 .
Reference 2:
    thorpe, p.; castaner, j.; mexiletine. drugs fut 1976, 1, 4, 180.

Route 2
the addition reaction of 2,6-dimethylphenol (ii) to (s)-2-methyloxirane (i) by means of naoh in acetonitrile gives (s)-1-(2,6-dimethylphenoxy)-2-propanol (iii), which is condensed with phthalimide (iv) by means of dead and pph3 (with inversion of configuration) yielding n-[2-(2,6-dimethylphenoxy)-1(r)-methylethyl]phthalimide (v). finally, this compound is treated with hydrazine and acetic acid in methanol to eliminate the phthalimido group.
List of intermediates No.
1-[(2-aminoethyl)amino]-3-(2-chlorophenoxy)-2-propanol (iv)
benzyl (2s,3s)-2-hexyl-3-hydroxy-5-oxopentadecanoate (i)
methyl 2-(4-acetyl-2-methylphenoxy)acetate (ii)
methyl 2-[4-(acetoxy)-2-methylphenoxy]acetate (iii)
methyl 2-(4-hydroxy-2-methylphenoxy)acetate (v)
Reference 1:
    carocci, a.; et al.; facile entry to (-)-(r)- and (+)-(s)-mexiletine. chirality 2000, 12, 3, 103.

Route 3
the addition reaction of 2,6-dimethylphenol (ii) to (r)-2-methyloxirane (i) by means of naoh in acetonitrile gives (r)-1-(2,6-dimethylphenoxy)-2-propanol (iii), which is condensed with phthalimide (iv) by means of dead and pph3 (with inversion of configuration) yielding n-[2-(2,6-dimethylphenoxy)-1(s)-methylethyl]phthalimide (v). finally, this compound is treated with hydrazine and acetic acid in methanol to eliminate the phthalimido group.
List of intermediates No.
1-[(2-aminoethyl)amino]-3-(2-chlorophenoxy)-2-propanol (iv)
benzyl (2s,3s)-2-hexyl-3-hydroxy-5-oxopentadecanoate (i)
methyl 2-(4-acetyl-2-methylphenoxy)acetate (ii)
methyl 2-(4-[[(dimethylamino)carbothioyl]oxy]-2-methylphenoxy)acetate (iii)
methyl 2-(4-[[(dimethylamino)carbonyl]sulfanyl]-2-methylphenoxy)acetate (v)
Reference 1:
    carocci, a.; et al.; facile entry to (-)-(r)- and (+)-(s)-mexiletine. chirality 2000, 12, 3, 103.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名盐酸美西律;英文名Mexiletine hydrochloride;Mexitil;CAS[5370-01-4]

 
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