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【结 构 式】 
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【分子编号】47940 【品名】methyl (2S)-3-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]-2-methylpropanoate 【CA登记号】 |
【 分 子 式 】C16H22BrNO4 【 分 子 量 】372.25902 【元素组成】C 51.62% H 5.96% Br 21.46% N 3.76% O 17.19% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reaction of N-(tert-butoxycarbonyl)-L-alanine (I) with biphenyl-4-carbaldehyde (II) by means of oxalyl chloride and ZnCl2 or TsOH gives the oxazolidinone (III), which is alkylated with 4-bromobenzyl bromide (IV) and LHMDS in THF, yielding the alkylated compound (V). The opening of the oxazolidinone ring of (V) with LiOMe and NaHSO3 affords the aminopropionic ester (VI), which is cyclized again with 3,5-dichloroaniline (VII) by means of NaOMe in refluxing toluene to provide imidazolidinedione (VIII). Finally, this compound is methylated with MeI, NaOH and tetrabutylammonium bisulfate to give the target compound.
| 【1】 Farina, V.; Napolitano, E.; Crystallization-induced asymmetric transformations and self-regeneration of stereocenters (SROSC): Enantiospecific synthesis of alpha-benzylalanine and hydantoin BIRT-377. Tetrahedron Lett 2001, 42, 18, 3231. |
| 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) | 26450 | Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid | 15761-38-3 | C8H15NO4 | 详情 | 详情 |
| (II) | 28446 | [1,1'-biphenyl]-4-carbaldehyde | 3218-36-8 | C13H10O | 详情 | 详情 |
| (III) | 47938 | tert-butyl (2S,4S)-2-[1,1'-biphenyl]-4-yl-4-methyl-5-oxo-1,3-oxazolidine-3-carboxylate | C21H23NO4 | 详情 | 详情 | |
| (IV) | 16109 | 1-bromo-4-(bromomethyl)benzene; 4-Bromobenzyl bromide | 589-15-1 | C7H6Br2 | 详情 | 详情 |
| (V) | 47939 | tert-butyl (2S,4S)-2-[1,1'-biphenyl]-4-yl-4-(4-bromobenzyl)-4-methyl-5-oxo-1,3-oxazolidine-3-carboxylate | C28H28BrNO4 | 详情 | 详情 | |
| (VI) | 47940 | methyl (2S)-3-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]-2-methylpropanoate | C16H22BrNO4 | 详情 | 详情 | |
| (VII) | 26542 | 3,5-dichloroaniline | 626-43-7 | C6H5Cl2N | 详情 | 详情 |
| (VIII) | 47933 | (5R)-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-5-methyl-2,4-imidazolidinedione | C17H13BrCl2N2O2 | 详情 | 详情 |