(E)-3-(4-hydroxyphenyl)-2-propenamide -Drug Synthesis Database

【结构式】

【分子编号】27821

【品名】(E)-3-(4-hydroxyphenyl)-2-propenamide

【CA登记号】

【分子式】C₉H₉NO₂

【分子量】163.176

【元素组成】C 66.25% H 5.56% N 8.58% O 19.61%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VI)

The acylation of (E)-3-(4-hydroxyphenyl)-2-propenamide (VI) with acetic anhydride gives the 4[(E)-3-amino-3-oxo-1-propenyl]phenyl acetate (VII), which by reaction first with BF3 ethearate and then with ammonia is converted into the amidine (IV). Finally, this compound is condensed with 2-furylcarbonyl chloride (V) in pyridine and treated with methanesulfonic acid to afford the target sulfonate.

参考文献中间体

合成目标

【1】 Niwas, S.; Moore, R.; Kilpatrick, J.M.; Babu, Y.S.; Johnson, H.; Kellogg, D.; Development of novel inhibitors of complement and coagulation serine proteases. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 088.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	27820	(E)-3-(4-hydroxyphenyl)-2-propenimidamide		C₉H₁₀N₂O	详情	详情
(V)	26093	2-Furoyl chloride	527-69-5	C₅H₃ClO₂	详情	详情
(VI)	27821	(E)-3-(4-hydroxyphenyl)-2-propenamide		C₉H₉NO₂	详情	详情
(VII)	27822	4-[(E)-3-amino-3-oxo-1-propenyl]phenyl acetate		C₁₁H₁₁NO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIV)

Coupling of amino acid (VII) with dipeptide (XIII) employing EDC and HOAt yielded tripeptide (XIV). The Boc group of (XIV) was then deprotected with trifluoroacetic acid to furnish the title compound.

参考文献中间体

合成目标

【1】 Madsen, K.; Kruse hansen, T.; Watson, B.; Peschke, B.; Langeland Johansen, N.; Sehested Hansen, B.; Lau, J.; Thogersen, H.; Ankersen, M.; Petersen, H.; Synthesis and in vitro characterization of new growth hormone secretagogues derived form ipamorelin with dipeptidomimetic N-terminals. Eur J Med Chem 1999, 34, 5, 363.
【2】 Hansen, T.K.; Peschke, B.; Lau, J.; Lundt, B.F.; Ankersen, M.; Watson, B.; Madsen, K. (Novo Nordisk A/S); Cpds. with growth hormone releasing properties. JP 1999209336; JP 1999501054; JP 2000143613; US 6127391; WO 9723508 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VII)	37820	(E)-5-[(tert-butoxycarbonyl)(methyl)amino]-5-methyl-2-hexenoic acid	C₁₃H₂₃NO₄	详情	详情
(XIII)	27234	(2R)-N-[(1R)-1-benzyl-2-(methylamino)-2-oxoethyl]-N-methyl-2-(methylamino)-3-(2-naphthyl)propanamide	C₂₅H₂₉N₃O₂	详情	详情
(XIV)	27821	(E)-3-(4-hydroxyphenyl)-2-propenamide	C₉H₉NO₂	详情	详情

Extended Information