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【结 构 式】

【分子编号】35997

【品名】3-chloroglutamic acid

【CA登记号】

【 分 子 式 】C5H8ClNO4

【 分 子 量 】181.57556

【元素组成】C 33.07% H 4.44% Cl 19.53% N 7.71% O 35.25%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(II)

A new procedure for the synthesis of acivicin has been reported: The photochlorination of L-glutamic acid (I) gives 3-chloroglutamic acid (II); the corresponding diastereomers were separed by ion-exchange chromatography over Dowex-50 (H+). The reaction of (II) with benzyl chloroformate (III) affords N-carbobenzoxy-3-chloroglutamic acid (IV), which is anhydrized with dicyclohexylcarbodiimide to the corresponding protected anhydride (V). The reaction of (V) with lithium N-hydroxyphthalimide (VI) yields the phthalimidoxy derivative (VII), which is converted to the protected hydroxamic acid (VIII) by a treatment with hydroxylamine. The cyclization of (VIII) with triethylamine affords N-carbobenzoxytricholomic acid (IX), which is esterified with diphenyldiazomethane (X) giving the corresponding protected benzhydryl ester (Xl). The reaction of (XI) with dichloro-trisdimethylaminophosphorane (XII) yields the deprotected final compound (XIII), which is finally treated with trifluoroacetic acid and thioanisole (A).

1 Holladay, M.W.; Silverman, R.B.; Stereospecific total synthesis of the natural antitumor agent, (alphaS,5S)-alpha-maino-3-chloro-4,5-dihydro-5-isooxazoleacetic acid and its unnatural C-5 epimer. J Am Chem Soc 1981, 103, 24, 7357-58.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 19272 methyl phenyl sulfide; 1-(methylsulfanyl)benzene 100-68-5 C7H8S 详情 详情
(I) 28752 DL-2-Amino propane dicarboxylic acid; DL-2-Aminopentanoic acid; glutamic acid; DL-glutamic acid; (+/-)-2-Aminoglutaric acid 617-65-2 C5H9NO4 详情 详情
(II) 35997 3-chloroglutamic acid C5H8ClNO4 详情 详情
(III) 10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(IV) 35998 N-[(benzyloxy)carbonyl]-3-chloroglutamic acid C13H14ClNO6 详情 详情
(V) 35999 benzyl 4-chloro-2,6-dioxotetrahydro-2H-pyran-3-ylcarbamate C13H12ClNO5 详情 详情
(VI) 36000 lithium 1,3-dioxo-1,3-dihydro-2H-isoindol-2-olate C8H4LiNO3 详情 详情
(VII) 36001 lithium 2-[[(benzyloxy)carbonyl]amino]-3-chloro-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]-5-oxopentanoate C21H16ClLiN2O8 详情 详情
(VIII) 36002 N(2)-[(benzyloxy)carbonyl]-3-chloro-N(5)-hydroxyglutamine C13H15ClN2O6 详情 详情
(IX) 36003 2-[[(benzyloxy)carbonyl]amino]-2-(3-oxo-5-isoxazolidinyl)acetic acid C13H14N2O6 详情 详情
(XI) 36004 benzhydryl 2-[[(benzyloxy)carbonyl]amino]-2-(3-oxo-5-isoxazolidinyl)acetate C26H24N2O6 详情 详情
(XII) 36005 N-[dichloro[bis(dimethylamino)]phosphoranyl]-N,N-dimethylamine; N-[dichloro[bis(dimethylamino)]phosphoranyl]-N-methylmethanamine C6H18Cl2N3P 详情 详情
(XIII) 36006 benzhydryl 2-[[(benzyloxy)carbonyl]amino]-2-(3-chloro-4,5-dihydro-5-isoxazolyl)acetate C26H23ClN2O5 详情 详情
Extended Information