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【结 构 式】

【分子编号】61985

【品名】N-({(5S)-3-[4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

【CA登记号】

【 分 子 式 】C18H22FN3O5

【 分 子 量 】379.3883032

【元素组成】C 56.99% H 5.84% F 5.01% N 11.08% O 21.09%

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:(XII)

After protection of 1-benzyl-3-pyrrolidinone (I) as the corresponding ethylene ketal (II) with ethylene glycol and p-toluenesulfonic acid, N-benzyl group hydrogenolysis over Pearlman's catalyst provides the secondary amine (III). Subsequent condensation of amine (III) with 3,4-difluoronitrobenzene (IV) in hot DMF furnishes the N-aryl pyrrolidine (V). Reduction of the nitro group of (V) by transfer hydrogenation with ammonium formate and Pd/C leads to aniline (VI). This is further acylated with benzyl chloroformate producing carbamate (VII). Then, reaction of the lithium anion of carbamate (VII) with (R)-glycidyl butyrate (VIII) gives rise to oxazolidinone (IX). After conversion of alcohol (IX) to mesylate (X), the primary amine (XI) is obtained by Gabriel synthesis with potassium phthalimide, followed by hydrazinolysis. Acylation of amine (XI) with Ac2O produces amide (XII). The ethylene ketal of (XII) is then hydrolyzed with p toluenesulfonic acid in aqueous acetone, providing pyrrolidinone (XIII).

1 Paget, S.; Boggs, C.; Foleno, B.; Goldschmidt, R.; Hilliard, J.; Wira, E.; Bush, K.; Macielag, M.; Synthesis and antibacterial activity of pyrrolopyrimidine oxazolidinones. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1318.
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) 61976 1-(Phenylmethyl)-3-pyrrolidinone; 1-Benzyl-3-pyrrolidinone; 1-Benzyl-3-pyrrolidinon; N-Benzyl-3-pyrrolidone 775-16-6 C11H13NO 详情 详情
(II) 61977 7-benzyl-1,4-dioxa-7-azaspiro[4.4]nonane C13H17NO2 详情 详情
(III) 61978 1,4-dioxa-7-azaspiro[4.4]nonane C6H11NO2 详情 详情
(IV) 17013 1,2-difluoro-4-nitrobenzene; 3,4-Difluoronitrobenzene 369-34-6 C6H3F2NO2 详情 详情
(V) 61979 7-(2-fluoro-4-nitrophenyl)-1,4-dioxa-7-azaspiro[4.4]nonane C12H13FN2O4 详情 详情
(VI) 61980 4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-3-fluorophenylamine; 4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-3-fluoroaniline C12H15FN2O2 详情 详情
(VII) 61981 benzyl 4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-3-fluorophenylcarbamate C20H21FN2O4 详情 详情
(VIII) 18385 (2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate 60456-26-0 C7H12O3 详情 详情
(IX) 61982 (5R)-3-[4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-3-fluorophenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one C16H19FN2O5 详情 详情
(X) 61983 {(5R)-3-[4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl methanesulfonate C17H21FN2O7S 详情 详情
(XI) 61984 (5S)-5-(aminomethyl)-3-[4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-3-fluorophenyl]-1,3-oxazolidin-2-one C16H20FN3O4 详情 详情
(XII) 61985 N-({(5S)-3-[4-(1,4-dioxa-7-azaspiro[4.4]non-7-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide C18H22FN3O5 详情 详情
(XIII) 61986 N-({(5S)-3-[3-fluoro-4-(3-oxo-1-pyrrolidinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide C16H18FN3O4 详情 详情
Extended Information