[(5R)-2-oxo-3-(1H-pyrrol-1-yl)-1,3-oxazolidin-5-yl]methyl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】57808

【品名】[(5R)-2-oxo-3-(1H-pyrrol-1-yl)-1,3-oxazolidin-5-yl]methyl methanesulfonate

【CA登记号】

【分子式】C₉H₁₂N₂O₅S

【分子量】260.27076

【元素组成】C 41.53% H 4.65% N 10.76% O 30.74% S 12.32%

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：(VI)

Condensation of benzyl carbazate (I) with 2,5-dimethoxytetrahydrofuran (II) affords the N-benzyloxycarbonyl aminopyrrole (III). The lithiated derivative of (III) is condensed with (R)-glycidyl butyrate (IV) to furnish the chiral oxazolidinone (V). Alcohol (V) is converted to the corresponding mesylate (VI) with methanesulfonyl chloride and triethylamine. Finally, nucleophilic displacement of mesylate (VI) with sodium methoxide affords the target methyl ether.

参考文献中间体

合成目标

【1】 Massa, S.; Befani, O.; Esposito, M.; Sbardella, g.; Mai, A.; Turini, P.; Giovannini, V.; Mondovi, B.; 3-(1H-Pyrrol-1-yl)-2-oxazolidinones as reversible, highly potent, and selective inhibitors of monoamine oxidase type A. J Med Chem 2002, 45, 6, 1180.

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)	36108	benzyl 1-hydrazinecarboxylate	5331-43-1	C₈H₁₀N₂O₂	详情	详情
(II)	12132	2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether	696-59-3	C₆H₁₂O₃	详情	详情
(III)	57806	benzyl 1H-pyrrol-1-ylcarbamate		C₁₂H₁₂N₂O₂	详情	详情
(IV)	18385	(2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate	60456-26-0	C₇H₁₂O₃	详情	详情
(V)	57807	(5R)-5-(hydroxymethyl)-3-(1H-pyrrol-1-yl)-1,3-oxazolidin-2-one		C₈H₁₀N₂O₃	详情	详情
(VI)	57808	[(5R)-2-oxo-3-(1H-pyrrol-1-yl)-1,3-oxazolidin-5-yl]methyl methanesulfonate		C₉H₁₂N₂O₅S	详情	详情

Extended Information