5-oxotetrahydro-2-furancarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】37075

【品名】5-oxotetrahydro-2-furancarboxylic acid

【CA登记号】

【分子式】C₅H₆O₄

【分子量】130.10024

【元素组成】C 46.16% H 4.65% O 49.19%

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)

The reduction of N-benzyloxycarbonylprolinamide (I) with H2 over Pd/c in methanol gives prolinamide (II), which is condensed with N-benzyloxycarbonylhistidyl hydrazide (III) by means of NaNO2 - HCl in ethyl acetate yielding N-benzyloxycarbonylhistidylprolinamide (IV), The hydrolysis of (IV) with HBr in acetic acid affords histidylprolinamide (V), which is finally condensed with gamma-carboxy-gamma-butyrolactone (VI) by means of pentachlorophenol and dicyclohexylcarbodiimide in DMF. Compound (VI) is prepared by reaction of alpha-aminoglutaric acid (VII) with NaNO2 and 2N H2SO4 in water.

参考文献中间体

合成目标

【1】 Fujino, M.; Nishimura, P.; Nagawa, Y.; Fukuda, N.; US 4100152 .
【2】 Bauce, L.G.; Goren, H.J.; Synthesis of a series of residue 1-(pyroglutamic acid) analogs of thyrotropin releasing hormone. Intl J Pept Protein Res 1979, 14, 3, 216-226.
【3】 Larsen, S.D.; Stephenson, G.A.; Bunnell, C.A.; Reutzel, S.M.; Nichols, J.R. (Eli Lilly and Company); Intermediates and process for preparing olanzapine. US 6020487 .

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)	37076	benzyl (2R)-2-(aminocarbonyl)-1-pyrrolidinecarboxylate		C₁₃H₁₆N₂O₃	详情	详情
(II)	37077	(2R)-2-pyrrolidinecarboxamide		C₅H₁₀N₂O	详情	详情
(III)	36138	benzyl (1S)-2-hydrazino-1-(1H-imidazol-5-ylmethyl)-2-oxoethylcarbamate	49706-31-2	C₁₄H₁₇N₅O₃	详情	详情
(IV)	36139	benzyl (1S)-2-[(2S)-2-(aminocarbonyl)pyrrolidinyl]-1-(1H-imidazol-5-ylmethyl)-2-oxoethylcarbamate		C₁₉H₂₃N₅O₄	详情	详情
(V)	31253	(2S)-1-[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]-2-pyrrolidinecarboxamide		C₁₁H₁₇N₅O₂	详情	详情
(VI)	37075	5-oxotetrahydro-2-furancarboxylic acid		C₅H₆O₄	详情	详情
(VII)	28752	DL-2-Amino propane dicarboxylic acid; DL-2-Aminopentanoic acid; glutamic acid; DL-glutamic acid; (+/-)-2-Aminoglutaric acid	617-65-2	C₅H₉NO₄	详情	详情

Extended Information