tert-butyl (2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}-1-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】54636

【品名】tert-butyl (2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}-1-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₂₄H₃₄N₂O₆

【分子量】446.54384

【元素组成】C 64.55% H 7.67% N 6.27% O 21.5%

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 enantioselective condensation of N-Boc-L-prolinal (I) with the chiral 2-bromopropionyloxazolidinone (II) by means of Co(PPh3)4 in THF gives the chiral beta-hydroxyamide (III), which is methylated by means of trimethyloxonium tetrafluoroborate in dichloromethane to yield the methyl ether (IV). Finally, elimination of the chiral auxiliary of (IV) by means of LiOH and H2O2 affords the target amino acid intermediate (V) (see scheme no. 14950701a , intermediate (XV)).

参考文献中间体

合成目标

【1】 Pettit, G.R.; Grealish, M.P.; A cobalt-phosphine complex directed reformatsky approach to a stereospecific synthesis of the dolastatin 10 unit dolaproine (Dap). J Org Chem 2001, 66, 25, 8640.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	16734	(2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid	C₁₀H₁₇NO₄	详情	详情
(II)	54635	(4R,5S)-3-(2-bromopropanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one	C₁₃H₁₄BrNO₃	详情	详情
(III)	54614	tert-butyl (2S)-2-{(1R,2R)-1-hydroxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}-1-pyrrolidinecarboxylate	C₂₃H₃₂N₂O₆	详情	详情
(IV)	54636	tert-butyl (2S)-2-{(1R,2R)-1-methoxy-2-methyl-3-[(4R,5S)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-3-oxopropyl}-1-pyrrolidinecarboxylate	C₂₄H₃₄N₂O₆	详情	详情
(V)	23520	(2R,3R)-3-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-3-methoxy-2-methylpropionic acid	C₁₄H₂₅NO₅	详情	详情

Extended Information