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【结 构 式】

【分子编号】31452

【品名】ethyl (1S)-2-[(3S)-3-hydroxypyrrolidinyl]-2-oxo-1-phenylethylcarbamate

【CA登记号】

【 分 子 式 】C15H20N2O4

【 分 子 量 】292.33488

【元素组成】C 61.63% H 6.9% N 9.58% O 21.89%

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:(IV)

The condensation of (S)-phenylglycine (I) with ethyl chloroformate gave carbamate (II). After activation of (II) as the mixed anhydride with ethyl chloroformate in the presence of N-methylmorpholine, coupling with (S)-3-hydroxypyrrolidine (III) provided amide (IV). Reduction of both amide and carbamate groups of (IV) employing LiAlH4 in refluxing THF yielded diamine (V). This was finally condensed with diphenylacetyl chloride (VI) to furnish the title amide The condensation of (S)-phenylglycine (I) with ethyl chloroformate gave carbamate (II). After activation of (II) as the mixed anhydride with ethyl chloroformate in the presence of N-methylmorpholine, coupling with (S)-3-hydroxypyrrolidine (III) provided amide (IV). Reduction of both amide and carbamate groups of (IV) employing LiAlH4 in refluxing THF yielded diamine (V). This was finally condensed with diphenylacetyl chloride (VI) to furnish the title amide.

1 Ackermann, K.-A.; Budak, J.; Bathe, A.; Gottschlich, R.; Helfert, B.; Stein, I. (Merck Patent GmbH); Method for producing enantiomer-free N-methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidine-1-yl)ethyl]-2,2-diphenyl acetamide. DE 19827633; WO 9954298 .
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) 10716 (2S)-2-Amino-2-phenylethanoic acid; L-(+)-alpha-Phenylglycine 2935-35-5 C8H9NO2 详情 详情
(II) 12171 (2S)-2-[(Ethoxycarbonyl)amino]-2-phenylethanoic acid C11H13NO4 详情 详情
(III) 14490 (3R)tetrahydro-1H-pyrrol-3-ol; R-3-hydroxypyrrolidine 2799-21-5 C4H9NO 详情 详情
(IV) 31452 ethyl (1S)-2-[(3S)-3-hydroxypyrrolidinyl]-2-oxo-1-phenylethylcarbamate C15H20N2O4 详情 详情
(V) 31453 (3S)-1-[(2S)-2-(methylamino)-2-phenylethyl]-3-pyrrolidinol C13H20N2O 详情 详情
(VI) 23800 Diphenylacetyl chloride; 2,2-diphenylacetyl chloride 1871-76-7 C14H11ClO 详情 详情
Extended Information