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【结 构 式】

【分子编号】45064

【品名】ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate

【CA登记号】

【 分 子 式 】C11H8ClF3O3

【 分 子 量 】280.6306296

【元素组成】C 47.08% H 2.87% Cl 12.63% F 20.31% O 17.1%

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:(VI)

The synthesis of [14C]-labeled clinafloxacin hydrochloride has been reported: The chlorination of 2,4,5-trifluorobromobenzene (I) with lithium diisopropylamide and hexachlorocyclopentadiene gives 3-chloro-2,4,5-trifluorobromobenzene (II), which is carbonated with 14CO2 and butyllithium in ether yielding 3-chloro-2,4,5-trifluoro-3-chlorobenzoic acid (III). The reaction of (III) with SOCl2 affords the corresponding acyl chloride (IV), which is condensed with the dilithium salt of the malonic acid monoethyl ester (V) to give the benzoylacetate (VI). The reaction of (VI) with acetic anhydride and ethyl orthoformate at 120-30 C yields the ethoxymethylene derivative (VII), which by treatment with cyclopropylamine affords the aminomethylene compound (VIII). The cyclization of (VIII) by means of potassium tert-butoxide in DMSO gives 1-cyclopropyl-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carbox ylic acid (IX), which is condensed with N-[pyrrolidin-3(S)-yl]carbamic acid tert-butyl ester by means of triethylamine in hot DMSO yielding the protected final product (XI). Finally, this compound is deprotected with 12N HCl in THF.

1 Huang, C.C.; Ekhato, I.V.; A synthetic approach to carbon-14 labeled anti-bacterial naphthyridine and quinolone carboxylic acids. J Label Compd Radiopharm 1993, 33, 9, 869.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12263 Cyclopropylamine; Cyclopropanamine 765-30-0 C3H7N 详情 详情
(I) 11676 1-Bromo-2,4,5-trifluorobenzene 327-52-6 C6H2BrF3 详情 详情
(II) 11677 1-Bromo-3-chloro-2,4,5-trifluorobenzene C6HBrClF3 详情 详情
(III) 11678 3-Chloro-2,4,5-trifluorobenzoic acid C7H2ClF3O2 详情 详情
(III) 45062 3-chloro-2,4,5-trifluorobenzoic acid C7H2ClF3O2 详情 详情
(IV) 11679 3-Chloro-2,4,5-trifluorobenzoyl chloride C7HCl2F3O 详情 详情
(IV) 45063 3-chloro-2,4,5-trifluorobenzoyl chloride C7HCl2F3O 详情 详情
(V) 11680 Lithium (1-carboxylato-2-ethoxy-2-oxoethyl)lithium C5H6Li2O4 详情 详情
(VI) 11681 ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate 101987-86-4 C11H8ClF3O3 详情 详情
(VI) 45064 ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate C11H8ClF3O3 详情 详情
(VII) 11682 ethyl (Z)-2-(3-chloro-2,4,5-trifluorobenzoyl)-3-ethoxy-2-propenoate C14H12ClF3O4 详情 详情
(VII) 45065 ethyl (Z)-2-(3-chloro-2,4,5-trifluorobenzoyl)-3-ethoxy-2-propenoate C14H12ClF3O4 详情 详情
(VIII) 11683 ethyl (E)-2-(3-chloro-2,4,5-trifluorobenzoyl)-3-(cyclopropylamino)-2-propenoate C15H13ClF3NO3 详情 详情
(VIII) 45066 ethyl (E)-2-(3-chloro-2,4,5-trifluorobenzoyl)-3-(cyclopropylamino)-2-propenoate C15H13ClF3NO3 详情 详情
(IX) 11684 8-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid 101987-89-7 C13H8ClF2NO3 详情 详情
(IX) 45067 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C13H8ClF2NO3 详情 详情
(X) 11685 tert-butyl N-[(3S)tetrahydro-1H-pyrrol-3-yl]carbamate C9H18N2O2 详情 详情
(XI) 11686 7-[(3S)-3-[(tert-Butoxycarbonyl)amino]tetrahydro-1H-pyrrol-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C22H25ClFN3O5 详情 详情
(XI) 45068 7-[(3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidinyl]-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C22H25ClFN3O5 详情 详情
Extended Information