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【结 构 式】

【分子编号】42279

【品名】2,2,2-trichloroacetonitrile; Trichloromethylcyanide

【CA登记号】545-06-2

【 分 子 式 】C2Cl3N

【 分 子 量 】144.38684

【元素组成】C 16.64% Cl 73.66% N 9.7%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(I)

By condensation of D-glucopyranuronic acid methyl ester (I) with 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol (III) by means of Tms-OTf.

1 Taraporewala, I.B.; Kauffman, J.M.; Synthesis and structure activity relationships of anti-inflammatory 9,10-dihydro-9-oxo-2-acridine-alkanoic acids and 4-(2-carboxyphenyl)aminobenzenealkanoic acids. J Pharm Sci 1990, 79, 2, 173.
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) 42279 2,2,2-trichloroacetonitrile; Trichloromethylcyanide 545-06-2 C2Cl3N 详情 详情
(II) 42780 (trimethylsilyl)[(2S,3R,4S,5R,6S)-3,4,5-tris(acetoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl]oxonium trifluoromethanesulfonate C17H27F3O13SSi 详情 详情
(III) 42782 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol 59-02-9 C29H50O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

The cyclization of 2-(3,5-dimethoxyphenyl)glyoxal monohydrate (I) with methyl glyoxylate hemiacetal (II) and ammonium acetate in acetonitrile gives the imidazole derivative (III), which is protected with dihydrofuran (IV) and TsOH, yielding compound (V). The reduction of the ester group of (V) with LiBH4 affords the carbinol (VI), which is esterified with trichloroacetonitrile (VII) to provide the trichloroacetimidate (VIII). The condensation of (VIII) with ascomycin (IX) by means of CF3SO3H in N,N-dimethylpivalamide gives the adduct (X), which is finally deprotected with hot aqueous CF3SO3H.

1 Song, Z.; et al.; Highly chemoselective trichloroacetimidate-mediated alkylation of ascomycin: A convergent, practical synthesis of the immunosuppressant L-733,725. J Org Chem 1999, 64, 6, 1859.
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) 22759 1-(3,5-dimethoxyphenyl)-2,2-dihydroxy-1-ethanone C10H12O5 详情 详情
(II) 22764 methyl 2-hydroxy-2-methoxyacetate 19757-97-2 C4H8O4 详情 详情
(III) 22765 methyl 4-(3,5-dimethoxyphenyl)-1H-imidazole-2-carboxylate C13H14N2O4 详情 详情
(IV) 22766 2,3-dihydrofuran 1191-99-7 C4H6O 详情 详情
(V) 22767 methyl 4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazole-2-carboxylate C17H20N2O5 详情 详情
(VI) 22768 [4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazol-2-yl]methanol C16H20N2O4 详情 详情
(VII) 42279 2,2,2-trichloroacetonitrile; Trichloromethylcyanide 545-06-2 C2Cl3N 详情 详情
(VIII) 22769 [4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazol-2-yl]methyl 2,2,2-trichloroethanimidoate C18H20Cl3N3O4 详情 详情
(IX) 14951 (1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetron C43H69NO12 详情 详情
(X) 42280 (1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-12-[(E)-2-((1R,3R,4R)-4-[[4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazol-2-yl]methoxy]-3-methoxycyclohexyl)-1-methylethenyl]-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,2 C59H87N3O15 详情 详情

合成路线3

该中间体在本合成路线中的序号:(IX)

The cyclization of 2-(3,5-dimethoxyphenyl)glyoxal monohydrate (I) with methyl glyoxylic acid (II) and ammonium acetate in acetonitrile gives the aryl imidazole (III), which is protected with dihydrofuran (IV) and Ts-OH, yielding compound (V). The regioselective lithiation of (V) with n-BuLi, followed by reaction with labeled 14CO2 provides the carboxylic acid (VI), which is esterified with MeI and CaO in DMSO to furnish the methyl ester (VII). The reduction of the ester group of (VII) with LiBH4 affords the carbinol (VIII), which is esterified with trichloroacetonitrile (IX) to provide the trichloroacetimidate (X).

1 Egan, M.A.M.; et al.; Carbon-14 labeling of a potential new immunoregulant agent. J Label Compd Radiopharm 2000, 43, 11, 1095.
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) 22759 1-(3,5-dimethoxyphenyl)-2,2-dihydroxy-1-ethanone C10H12O5 详情 详情
(II) 15618 2-Oxoacetic acid; Glyoxylic Acid 298-12-4 C2H2O3 详情 详情
(III) 42281 4-(3,5-dimethoxyphenyl)-1H-imidazole; 3-(1H-imidazol-4-yl)-5-methoxyphenyl methyl ether C11H12N2O2 详情 详情
(IV) 22766 2,3-dihydrofuran 1191-99-7 C4H6O 详情 详情
(V) 42282 4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazole; 3-methoxy-5-(1-tetrahydro-2-furanyl-1H-imidazol-4-yl)phenyl methyl ether C15H18N2O3 详情 详情
(VI) 42283 lithium 4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazole-2-carboxylate C16H17LiN2O5 详情 详情
(VI) 45345 lithium 4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazole-2-carboxylate C16H17LiN2O5 详情 详情
(VII) 22767 methyl 4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazole-2-carboxylate C17H20N2O5 详情 详情
(VII) 45346 methyl 4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazole-2-carboxylate C17H20N2O5 详情 详情
(VIII) 22768 [4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazol-2-yl]methanol C16H20N2O4 详情 详情
(VIII) 45347 [4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazol-2-yl]methanol C16H20N2O4 详情 详情
(IX) 42279 2,2,2-trichloroacetonitrile; Trichloromethylcyanide 545-06-2 C2Cl3N 详情 详情
(X) 22769 [4-(3,5-dimethoxyphenyl)-1-tetrahydro-2-furanyl-1H-imidazol-2-yl]methyl 2,2,2-trichloroethanimidoate C18H20Cl3N3O4 详情 详情
Extended Information