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【结 构 式】

【分子编号】58562

【品名】2-[3-(3-bromopropoxy)phenyl]acetic acid

【CA登记号】

【 分 子 式 】C11H13BrO3

【 分 子 量 】273.12642

【元素组成】C 48.37% H 4.8% Br 29.26% O 17.57%

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:(V)

The title compound was prepared by solid-phase synthesis on a Sasrin resin. The silylated m-hydroxyphenylacetic acid (I) was attached to the resin using DCC and DMAP to yield the acid-bound resin (II). The silyl group of (II) was then removed by treatment of resin (II) with tetrabutylammonium fluoride in THF. The resultant phenol (III) was coupled to 3-bromo-1-propanol (IV) under Mitsunobu conditions to afford the bromide functionalized resin (V). Displacement of the bromide ion of (V) with 2,2-diphenylethylamine (VI) furnished the secondary amine (VII), which was subjected to reductive alkylation with aldehyde (VIII) in the presence of NaBH(OAc)3 to produce the resin-bound product (IX). Cleavage from the solid support employing trifluoroacetic acid in CH2Cl2 provided the target carboxylic acid.

1 Collins, J.L.; et al.; Identification of a nonsteroidal liver X receptor agonist through parallel array synthesis of tertiary amines. J Med Chem 2002, 45, 10, 1963.
2 Willson, T.M.; Collins, J.L.; Maloney, P.R.; Fivush, A.M.; Stewart, E.L. (GlaxoSmithKline plc); Chemical cpds.. WO 0224632 .
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),(II) 58560 2-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)acetic acid C14H22O3Si 详情 详情
(III) 58561 2-(3-hydroxyphenyl)acetic acid C8H8O3 详情 详情
(IV) 12573 3-Bromo-1-propanol; 3-Bromopropanol 627-18-9 C3H7BrO 详情 详情
(V) 58562 2-[3-(3-bromopropoxy)phenyl]acetic acid C11H13BrO3 详情 详情
(VI) 38962 2,2-diphenylethylamine; 2,2-diphenyl-1-ethanamine 3963-62-0 C14H15N 详情 详情
(VII) 58563 2-(3-{3-[(2,2-diphenylethyl)amino]propoxy}phenyl)acetic acid C25H27NO3 详情 详情
(VIII) 58564 2-chloro-3-trifluoromethyl benzaldehyde 93118-03-7 C8H4ClF3O 详情 详情
(IX) 58565 2-(3-{3-[[2-chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}phenyl)acetic acid C33H31ClF3NO3 详情 详情
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