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【结 构 式】

【分子编号】64239

【品名】(2S)-2-amino-1-[4-(benzyloxy)phenyl]-3-hydroxy-1-propanone

【CA登记号】

【 分 子 式 】C16H17NO3

【 分 子 量 】271.31592

【元素组成】C 70.83% H 6.32% N 5.16% O 17.69%

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 protected serine derivative (I) is converted into the corresponding Weinreb amide (II) upon coupling with N,O-dimethyl hydroxylamine in the presence of CBr4/PPh3. Reaction of (II) with 4-(benzyloxy)phenylmagnesium iodide (III) affords ketone (IV). Subsequent acidic cleavage of the protecting groups of (IV) leads to the hydroxy amino ketone (V). This is then acylated by oleoyl chloride (VI) to furnish amide (VII). Phosphitylation of the primary alcohol group of (VII) with di-tert-butyl N,N-diisopropylphosphoramidite, followed by oxidation with H2O2 gives rise to phosphate ester (VIII). The tert-butyl groups of (VIII) are finally cleaved by means of trifluoroacetic acid in CH2Cl2 to provide the title compound.

1 Heasley, B.H.; MacDonald, T.L.; Lynch, K.R.; Synthesis and biological evaluation of lysophosphatidic acid (LPA) antagonists. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 248.
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) 64236 (4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid C11H19NO5 详情 详情
(II) 55202 tert-butyl (4R)-4-{[methoxy(methyl)amino]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate C13H24N2O5 详情 详情
(III) 64237 [4-(benzyloxy)phenyl](iodo)magnesium C13H11IMgO 详情 详情
(IV) 64238 tert-butyl (4S)-4-[4-(benzyloxy)benzoyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate C24H29NO5 详情 详情
(V) 64239 (2S)-2-amino-1-[4-(benzyloxy)phenyl]-3-hydroxy-1-propanone C16H17NO3 详情 详情
(VI) 28280 Oleoyl chloride; (E)-9-Octadecenoyl chloride C18H33ClO 详情 详情
(VII) 64240 (Z)-N-[(1S)-2-[4-(benzyloxy)phenyl]-1-(hydroxymethyl)-2-oxoethyl]-9-octadecenamide C34H49NO4 详情 详情
(VIII) 64241 (2S)-3-[4-(benzyloxy)phenyl]-2-[(Z)-9-octadecenoylamino]-3-oxopropyl di(tert-butyl) phosphate C42H66NO7P 详情 详情
Extended Information