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【结 构 式】

【分子编号】25981

【品名】2-(4-[2-[[(4-fluoroanilino)carbonyl](heptyl)amino]ethyl]phenoxy)-2-methylpropionic acid

【CA登记号】

【 分 子 式 】C26H35FN2O4

【 分 子 量 】458.5733832

【元素组成】C 68.1% H 7.69% F 4.14% N 6.11% O 13.96%

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:(XII)

The N-protection of 4-(2-aminoethyl)phenol (I) with benzyl chloroformate gives the N-benzyloxycarbonyl derivative (II), which is condensed with 1-methyl-1-(trichloromethyl)ethanol (III) by means of NaOH in acetone yielding the phenoxyisobutyric acid (IV). The deprotection of the amino group of (IV) by hydrogenation over Pd/C affords the ethylamino derivative (V), which is reprotected with 9-fluorenylmethoxycarbonyl protecting group to provide carbamate (VI). The acid group of (VI) is then coupled to a Sasrin polystyrene resin giving the N-protected resin (VII), which is deprotected with piperidine affording resin (VIII) with a free amino group, which is condensed with heptanoic acid (A) by means of DIC and HOBT to give the amide (IX). The reduction of the carbonyl group amide (IX) with BH3/THF yields the heptylamine (X), which is condensed with 4-fluorophenyl isocyanate (XI) to afford the urea (XII). Finally, this compound is treated with trifluoroacetic acid to eliminate the polystyrene resin and isolate the target compound. Alternatively, the heptylamine (X) can also be obtained directly by reductocondensation of the free amino group of the resin (VIII) with heptanal (B) by means of NaBH3CN.

1 Brown, P.J.; et al.; Generation of secondary alkyl amines on solid support by borane reduction. Application to the parallel synthesis of PPAR ligands. Synthesis 1997, 7, 778.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
13580 1-[(Chlorocarbonyl)oxy]benzene; phenyl chloroformate 1885-14-9 C7H5ClO2 详情 详情
(B) 25714 octanal 124-13-0 C8H16O 详情 详情
(A) 35032 heptanoic acid 111-14-8 C7H14O2 详情 详情
(I) 19988 4-(2-Aminoethyl)phenol; Tyramine 51-67-2 C8H11NO 详情 详情
(II) 25974 benzyl 4-hydroxyphenethylcarbamate C16H17NO3 详情 详情
(III) 25975 1,1,1-trichloro-2-methyl-2-propanol 57-15-8 C4H7Cl3O 详情 详情
(IV) 25976 2-[4-(2-[[(benzyloxy)carbonyl]amino]ethyl)phenoxy]-2-methylpropionic acid C20H23NO5 详情 详情
(V) 25977 2-[4-(2-aminoethyl)phenoxy]-2-methylpropionic acid C12H17NO3 详情 详情
(VI) 25978 2-[4-(2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethyl)phenoxy]-2-methylpropionic acid C27H27NO5 详情 详情
(VII) 25978 2-[4-(2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethyl)phenoxy]-2-methylpropionic acid C27H27NO5 详情 详情
(VIII) 25977 2-[4-(2-aminoethyl)phenoxy]-2-methylpropionic acid C12H17NO3 详情 详情
(IX) 25979 2-[4-[2-(heptanoylamino)ethyl]phenoxy]-2-methylpropionic acid C19H29NO4 详情 详情
(X) 25980 2-[4-[2-(heptylamino)ethyl]phenoxy]-2-methylpropionic acid C19H31NO3 详情 详情
(XI) 17977 1-Fluoro-4-isocyanatobenzene; 4-Fluorophenyl isocyanate 1195-45-5 C7H4FNO 详情 详情
(XII) 25981 2-(4-[2-[[(4-fluoroanilino)carbonyl](heptyl)amino]ethyl]phenoxy)-2-methylpropionic acid C26H35FN2O4 详情 详情
Extended Information