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药物详细合成路线

Name Flomoxef sodium;FMOX;6315-S;Flumarin
Chemical Name (-)-(6R,7R)-7-[2-(Difluoromethylthio)acetamido]-7-methoxy-3-[[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thiomethyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt
      7beta-[(2-(Difluoromethylthio)acetamido]-7alpha-methoxy-3-[[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thiomethyl]-1-oxa-3-cephem-4-carboxylic acid sodium salt
CAS 92823-03-5
Related CAS 92823-00-2 (free acid)
Formula C15H17F2N6NaO7S2
Structure
Formula Weight 518.45334
Stage 上市-1988
Company Shionogi (Originator), ISF (Licensee)
Activity/Mechanism Antibiotics, ANTIINFECTIVE THERAPY, Oxacephems
Syn. Route 1
Route 1
this compound can be prepared by the route shown in scheme:reaction of chlorodifluoromethane (freon 22) with ethyl thioglycolate (ii) in the presence of ethanolic sodium ethoxide gives ethyl 2-(difluoro-methylthio)acetate (iii), which is hydrolyzed with aqueous potassium hydroxide to yield 2-(difluoromethylthio)acetic acid (iv). substitution of diphenylmethyl-7alpha-benzamido-3-chloromethyl-1-oxa-3-cephem-4-carboxylate (v), an important intermediate for production of latamoxef, with 1-(2-hydroxyethyl)-1h-tetrazole-5-thiol (vi) in the presence of sodium methoxide, followed by protection of the hydroxyl group by means of p-methylbenzyl chlorocarbonate (vii) and pyridine, gives diphenylmethyl 7alpha-benzamido-3-[[1-[2-(p-methylbenzyloxycarbonyloxy)ethyl-1h-tetrazol-5-yl]thiomethyl]-1-oxa-3-cephem-4-carboxylate (viii). methoxylation of (viii) with tert-butylhypochlorite and lithium methoxide, followed by the conventional side-chain cleavage with phosphorus pentachloride pyridine methanol, affords diphenylmethyl 7beta-amino-7alpha-methoxy-3-[[1-[2-(p-methylbenzyloxycarbonyloxy)ethyl]-1h-tetrazol-5-yl]thiomethyl]-1-oxa-3-cephem-4-carboxylate (x). this amine (ix) is condensed with the acid (iv) by means of phosphoryl chloride and pyridine fo yield diphenyl-methyl 7beta[2-(dfluoromelhylthio)acetamido]-7alpha-methoxy-3-[[1-[2-(p-methylbenzyloxycarbonyloxy)ethyl]-1h-tetrazol-5 yl)thiomethyl]-1-oxa-3-cephem 4-carboxylate (x), which undergoes deprotection with stannic chloride and anisole, neutralization with aqueous sodium bicarbonate and lyophilization giving the sodium salt (xi).
List of intermediates No.
2-(allyloxy)-2-(2,4-dichlorophenyl)acetic acid (i)
2-(allyloxy)-2-(2,4-dichlorophenyl)-1-ethanol (iv)
3-(allyloxy)-3-(2,4-dichlorophenyl)propyl methanesulfonate (v)
1-(2,4-dichlorophenyl)-1-ethanone; 2,4-dichloroaetophenone (vi)
2-bromo-1-(2,4-dichlorophenyl)-1-ethanone (vii)
(1r,2r)-2-amino-1-[4-(methylsulfonyl)phenyl]-1,3-propanediol (viii)
2-[(1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-1h-isoindole-1,3(2h)-dione (ix)
2-[(1s,2r)-1-(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]-1h-isoindole-1,3(2h)-dione (x)
methyl 2,2-dichloroacetate (iii)
2-(4-hydroxyphenyl)-1-benzothiophen-6-ol (ii)
Reference 1:
    tsuji, t.; et al.; synthesis and antibacterial activity of 6315-s, a new member of the oxacephem antibiotic. j antibiot 1984, 38, 4, 466.
Reference 2:
    castaner, j.; serradell, m.n.; flomoxef sodium. drugs fut 1986, 11, 6, 452.

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氟氧头孢钠;英文名Flomoxef sodium;FMOX;6315-S;Flumarin;CAS[92823-03-5]

 
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