benzyl (3R)-3-amino-2-oxo-1-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】47798

【品名】benzyl (3R)-3-amino-2-oxo-1-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₁₂H₁₄N₂O₃

【分子量】234.25484

【元素组成】C 61.53% H 6.02% N 11.96% O 20.49%

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：(XXI)

The reaction of D-methionine (XIV) with Boc2O in dioxane gives the N-protected methionine (XV), which is treated with Boc2O, pyridine and ammonium bicarbonate to yield the methioninamide (XVI). The reaction of (XVI) with benzyl chloroformate (XVII) by means of BuLi in DMF/pyridine affords the carbamate (XVIII), which is treated with methyl iodide in acetone to provide the sulfonium salt (XIX). The cyclization of (XIX) by means of Dowex 2XB-400 (OH form) in acetonitrile gives the N-protected pyrrolidinone (XX), which is deprotected with HCl in dioxane to yield the amino compound (XXI). Finally, this compound is acylated with methyl trifluoroacetate (XXII) and NMM in dichloromethane to afford the target pyrrolidinone intermediate (XXIII).

参考文献中间体

合成目标

【1】 Dowle, M.D.; Finch, H.; Harrison, L.A.; Inglis, G.G.A.; Johnson, M.R.; Macdonald, S.J.F.; Shah, P.; Smith, R.A. (Glaxo Wellcome plc); Pyrrolopyrrolone derivs. as inhibitors of neutrophil elastase. EP 0891362; JP 2000507950; US 5994344; WO 9736903 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	26695	D-methionine	348-67-4	C₅H₁₁NO₂S	详情	详情
(XV)	26710	(2R)-2-[(tert-butoxycarbonyl)amino]-4-(methylsulfanyl)butyric acid	5241-66-7	C₁₀H₁₉NO₄S	详情	详情
(XVI)	26696	tert-butyl (1R)-1-(aminocarbonyl)-3-(methylsulfanyl)propylcarbamate		C₁₀H₂₀N₂O₃S	详情	详情
(XVII)	10101	Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene	501-53-1	C₈H₇ClO₂	详情	详情
(XVIII)	26697	benzyl (2R)-2-[(tert-butoxycarbonyl)amino]-4-(methylsulfanyl)butanoylcarbamate		C₁₈H₂₆N₂O₅S	详情	详情
(XIX)	26698	[(3R)-4-[[(benzyloxy)carbonyl]amino]-3-[(tert-butoxycarbonyl)amino]-4-oxobutyl](dimethyl)sulfonium iodide		C₁₉H₂₉IN₂O₅S	详情	详情
(XX)	26699	benzyl (3R)-3-[(tert-butoxycarbonyl)amino]-2-oxo-1-pyrrolidinecarboxylate		C₁₇H₂₂N₂O₅	详情	详情
(XXI)	47798	benzyl (3R)-3-amino-2-oxo-1-pyrrolidinecarboxylate		C₁₂H₁₄N₂O₃	详情	详情
(XXII)	47799	Methyl trifluoroacetate; Trifluoroacetic acid methyl ester; methyl 2,2,2-trifluoroacetate	431-47-0	C₃H₃F₃O₂	详情	详情
(XXIII)	26700	benzyl (3R)-2-oxo-3-[(2,2,2-trifluoroacetyl)amino]-1-pyrrolidinecarboxylate		C₁₄H₁₃F₃N₂O₄	详情	详情

Extended Information