(2S,4R)-1-(tert-butoxycarbonyl)-4-(2-naphthylmethoxy)-2-pyrrolidinecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】35613

【品名】(2S,4R)-1-(tert-butoxycarbonyl)-4-(2-naphthylmethoxy)-2-pyrrolidinecarboxylic acid

【CA登记号】

【分子式】C₂₁H₂₅NO₅

【分子量】371.43324

【元素组成】C 67.91% H 6.78% N 3.77% O 21.54%

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：(III)

Alkylation of N-Boc-4-(R)-hydroxyproline (I) with 2-(bromomethyl)-naphthalene (II) in the presence of NaH afforded the (naphthylmethyl) ether (III). N-Boc-norvaline (IV) was converted to the benzyl ester (V) by treatment with benzyl bromide and DBU. Subsequent acid cleavage of the Boc group of (V) yielded norvaline benzyl ester (VI). This was coupled with proline derivative (III) using HATU to give the protected dipeptide (VII).

参考文献中间体

合成目标

【1】 Rancourt, J.; Tsantrizos, Y.; Simoneau, B.; Wernic, D.; Poupart, M.-A.; Llinas-Brunet, M. (Boehringer Ingelheim (Canada) Ltd.); Hepatitis C inhibitor peptides. EP 1003775; WO 9907733 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
(I)	16094	(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;1-(tert-butoxycarbonyl)-4®-hydroxy-L-proline;(2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxytetrahydro-1H-pyrrole-2-carboxylic acid	16094	C₁₀H₁₇NO₅	详情	详情
(II)	35612	2-(bromomethyl)naphthalene	939-26-4	C₁₁H₉Br	详情	详情
(III)	35613	(2S,4R)-1-(tert-butoxycarbonyl)-4-(2-naphthylmethoxy)-2-pyrrolidinecarboxylic acid		C₂₁H₂₅NO₅	详情	详情
(IV)	35614	(2S)-2-[(tert-butoxycarbonyl)amino]pentanoic acid	53308-95-5	C₁₀H₁₉NO₄	详情	详情
(V)	35615	benzyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanoate		C₁₇H₂₅NO₄	详情	详情
(VI)	35616	benzyl (2S)-2-aminopentanoate		C₁₂H₁₇NO₂	详情	详情
(VII)	35617	tert-butyl (2S,4R)-2-[([(1S)-1-[(benzyloxy)carbonyl]butyl]amino)carbonyl]-4-(2-naphthylmethoxy)-1-pyrrolidinecarboxylate		C₃₃H₄₀N₂O₆	详情	详情

Extended Information