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【结 构 式】

【分子编号】25893

【品名】(2R)-2-[methyl(2-phenylacetyl)amino]-3-(2-naphthyl)propanamide

【CA登记号】

【 分 子 式 】C22H22N2O2

【 分 子 量 】346.42896

【元素组成】C 76.28% H 6.4% N 8.09% O 9.24%

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 acylation of 3-(2-naphthyl)-D-alanine (I) with phenylacetyl chloride (II) and bis(trimethylsilyl)acetamide in THF gives the expected N-phenylacetyl derivative (III), which is methylated with NaH and methyl iodide in THF yielding the N-methyl derivative (IV). The reaction of (IV) with 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (WSC), HOBT and ammonium hydroxide affords the corresponding alaninamide (V), which by reaction with bis(trifluoroacetoxy)iodobenzene (BTI) in acetonitrile is converted into the monoacylated gemdiamine (VI). The condensation of (VI) with cis-2-(1H-indol-3-ylcarboxamido)cyclohexanecarboxylic acid (VII) by means of WSC and HOBT in DMF affords the target compound as a diastereomeric mixture that is separated by preparative RP-HPLC.

1 Sisto, A.; Fincham, C.; Potier, E.; Manzini, S.; Arcamone, F.; Lombardi, P. (Malesci Ist. Farmacobiol. SpA; Menarini Industrie Farma Riunite srl); Tachykinin antagonists. EP 0731790; JP 1997506348; US 5760248; WO 9515311 .
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) 21016 (2R)-2-amino-3-(2-naphthyl)propionic acid; D-3-(2-Naphthyl)alanine 76985-09-6 C13H13NO2 详情 详情
(II) 25890 2-phenylacetyl chloride;Phenylacetyl chloride;Phenacetyl chloride;Benzeneacetyl chloride 103-80-0 C8H7ClO 详情 详情
(III) 25891 (2R)-3-(2-naphthyl)-2-[(2-phenylacetyl)amino]propionic acid C21H19NO3 详情 详情
(IV) 25892 (2R)-2-[methyl(2-phenylacetyl)amino]-3-(2-naphthyl)propionic acid C22H21NO3 详情 详情
(V) 25893 (2R)-2-[methyl(2-phenylacetyl)amino]-3-(2-naphthyl)propanamide C22H22N2O2 详情 详情
(VI) 25894 N-[(1R)-1-amino-2-(2-naphthyl)ethyl]-N-methyl-2-phenylacetamide C21H22N2O 详情 详情
(VII) 25895 (1R,2S)-2-[(1H-indol-3-ylcarbonyl)amino]cyclohexanecarboxylic acid C16H18N2O3 详情 详情
Extended Information