合成路线:Tetrahydrofurfurylamine (XLVII) was converted into the corresponding phthalimide (XLVIII) by reaction of phthalic anhydride (V) in boiling chloroform.Subsequent ruthenium-catalyzed oxidation of (XLVIII) produced keto acid (XI),along with a pentanolide by-product,which was removed by column chromatography.Finally,acid hydrolysis of (XI) led to the desired compound.A closely related strategy was based in the ruthenium oxidation of N-benzoyl tetrahydrofurfurylamine (LXX),prepared from amine (XLVII) and benzoyl chloride (XLIX),to afford 5-benzoylaminolevulinic acid (XXXV),which was then hydrolyzed in boiling 6 N HCl .
参考文献标题:Method of preparing an acid additional salt of delta-aminolevulinic acid
文献作者:Matsumoto,K.; Kawakami,H.; Koseki,K.; Ebata,T.; Matsushita,H.(Japan Tobacco Inc.)
参考来源:US 5284973
合成路线:A related method was based on the oxidation of N-furfuryl phthalimide (LXXI) under irradiation by light in the presence of oxigen gas and a sensitizer,such as Rose Bengal,to afford the 2,5-dihydrofuranone (LXXII) along with its ring-opened isomer (LXXIII).Subsequent catalytic hydrogenation provided phthalimidolevulinic acid (XI),which was then subjected to acidic hydrolysis.Butenolide (LXXII) was also obtained by the photooxygenation of 5-phthalimidomethyl)furfural (LXXIV).Reduction of (LXXII) to phthalimidolevulinic acid (XI) was accomplished using zinc dust in HOAc under sonication.
参考文献标题:Process for preparing 5-aminolevulinic acid
文献作者:Shimizu,T.; Takeya,H.; Ueki,H.
参考来源:US 5380935
合成路线:In a variation of the earlier methods,methyl 5-bromolevulinate (XLIII) was prepared by bromination of levulinic acid (XLII) in methanol.Reaction of bromo ketone (XLIII) with NaN3 in cold DMF provided azide (LXXV).Simultaneous azide reduction and methyl ester hydrolysis was then accomplished by catalytic hydrogenation in the presence of HCl.A further related method consisted in the alkylation of sodium diformylamide (LXXVI) with methyl 5-bromolevulinate (XLIII) in several different solvents to afford the N,N-diformylamino ester (LXXVII),which was finally hydrolyzed under acidic conditions.
参考文献标题:Synthesis of an acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters
文献作者:Moens,L.
参考来源:US 5907058
合成路线:In a variation of the earlier methods,methyl 5-bromolevulinate (XLIII) was prepared by bromination of levulinic acid (XLII) in methanol.Reaction of bromo ketone (XLIII) with NaN3 in cold DMF provided azide (LXXV).Simultaneous azide reduction and methyl ester hydrolysis was then accomplished by catalytic hydrogenation in the presence of HCl.A further related method consisted in the alkylation of sodium diformylamide (LXXVI) with methyl 5-bromolevulinate (XLIII) in several different solvents to afford the N,N-diformylamino ester (LXXVII),which was finally hydrolyzed under acidic conditions.
参考文献标题:Synthesis of delta-aminolevulinic acid
文献作者:Moens,L.
参考来源:ACS Symp Ser 2001,78437
合成路线:The condensation of the labeled glycine (I) with phthalic anhydride (II) by heating at 160 C gives the labeled phthalimido acetic acid (III),which is treated with refluxing SOCl2 to yield the acyl chloride (IV).The condensation of (IV) with 3-iodopropionic acid ethyl ester (V) by means of the Zn/Cu couple and Pd(PPh3)4 in hot toluene affords the labeled 5-phthalimido-levulinate (VI),which is finally treated with refluxing 6N HCl to provide the target labeled aminolevulinic acid.
参考文献标题:Synthesis of 13C and 15N multilabeled 5-aminolevulinic acid
文献作者:Iida,K.; Kajiwara,M.
参考来源:J Label Compd Radiopharm 2002,45(2),139
合成路线:Methyl acetylacrylate (III) was obtained by bromination of methyl levulinate (I) followed by dehydrohalogenation of the resultant bromide (II).Isonitrosation of ketone (III) by means of ethyl nitrite in ethereal HCl produced the alpha-keto oxime (IV).Reduction of oxime (IV) and simultaneous ester hydrolysis by means of Sn/SnCl2 in concentrated HCl led to the target 5-aminolevulinic acid.
参考文献标题:The hydrogenation of oxaloacetone.A new synthesis of beta-thiolimidazolylpropionic acid
文献作者:Corwin,A.H.; Wynn,R.W.
参考来源:J Org Chem 1950,15203
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