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【结 构 式】

【分子编号】27910

【品名】chloro(phenyl)magnesium

【CA登记号】100-59-4

【 分 子 式 】C6H5ClMg

【 分 子 量 】136.8634

【元素组成】C 52.66% H 3.68% Cl 25.9% Mg 17.76%

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:(I)

The synthesis of ring labeled [14C]-atorvastatin has been described: The Grignard reaction of phenylmagnesium chloride (I) with [14C]-labeled CO2 (II) in THF/ethyl ether gives the benzoic acid (III), which is reduced with LiAlH4 in ethyl ether to the benzyl alcohol (IV). The oxidation of (IV) with pyridinium dichromate affords the benzaldehyde (V), which is condensed with the isobutyrylacetamide (VI) by means of beta-alanine in acetic acid yielding a mixture of the cis- and trans-benzylidene derivatives (VII). The condensation of (VII) with 4-fluorobenzaldehyde (VIII) by means of triethylamine and a thiazolium bromide catalyst affords the 1,4-dione (IX), which is cyclized with the chiral amino ester (X) in hot heptane/toluene/THF providing the protected pyrroloheptanoic ester (XI). The deprotection of (XI) in acidic medium, followed by the hydrolysis of the ester group with NaOH affords the sodium salt (XII), which is finally treated with calcium acetate in THF/water.

1 Woo, P.W.K.; et al.; Atorvastatin, an HMG-CoA reductase inhibitor and efficient lipid-regulating agent. Part I. Synthesis of ring-labeled [C-14] atorvastatin. J Label Compd Radiopharm 1999, 42, 2, 121.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 27910 chloro(phenyl)magnesium 100-59-4 C6H5ClMg 详情 详情
(III) 10202 Benzoic acid 65-85-0 C7H6O2 详情 详情
(III) 45234 benzoic acid C7H6O2 详情 详情
(IV) 18710 Benzyl alcohol; Phenylmethanol 100-51-6 C7H8O 详情 详情
(IV) 45235 phenylmethanol C7H8O 详情 详情
(V) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(V) 44663 benzaldehyde C7H6O 详情 详情
(VI) 15448 4-Methyl-3-oxo-N-phenylpentanamide; 4-Methyl-3-oxopentanoic acid anilide 124401-38-3 C12H15NO2 详情 详情
(VII) 15450 (Z)-2-isobutyryl-N,3-diphenyl-2-propenamide 125971-57-5 C19H19NO2 详情 详情
(VII) 45236 (Z)-2-isobutyryl-N,3-diphenyl-2-propenamide C19H19NO2 详情 详情
(VIII) 12337 4-fluorobenzaldehyde 459-57-4 C7H5FO 详情 详情
(IX) 15426 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide 125971-96-2 C26H24FNO3 详情 详情
(IX) 45237 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide C26H24FNO3 详情 详情
(X) 15444 (4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate; (4R-Cis)-1,1-Dimethylethyl-6-aminoethyl-2,2-dimethyl-1,3-dioxoane-4-acetate 125995-13-3 C14H27NO4 详情 详情
(XI) 15452 tert-butyl 2-((4R,6R)-6-[2-[3-(anilinocarbonyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl)acetate C40H47FN2O5 详情 详情
(XI) 45238 tert-butyl 2-((4R,6R)-6-[2-[3-(anilinocarbonyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl)acetate C40H47FN2O5 详情 详情
(XII) 27911 sodium (3R,5R)-7-[3-(anilinocarbonyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate C33H34FN2NaO5 详情 详情
(XII) 45239 sodium (3R,5R)-7-[3-(anilinocarbonyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate C33H34FN2NaO5 详情 详情
Extended Information