(3R,6S)-6-[(tert-butoxycarbonyl)amino]-7-oxoazepanyl cyclohexanecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】54666

【品名】(3R,6S)-6-[(tert-butoxycarbonyl)amino]-7-oxoazepanyl cyclohexanecarboxylate

【CA登记号】

【分子式】C₁₈H₃₀N₂O₅

【分子量】354.44668

【元素组成】C 61% H 8.53% N 7.9% O 22.57%

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)

Cyclization of (5R)-5-hydroxy-L-lysine (VIII) by means of EDC and HOBt afforded the caprolactam (IX). The amino group of (IX) was then protected as the N-Boc derivative (X) by treatment with Boc2O. Hydroxyl group acylation in (X) with cyclohexanecarbonyl chloride (XI) produced ester (XII). The Boc protecting group of (XII) was then removed by treatment with trifluoroacetic acid, yielding the aminocaprolactam (XIII). Coupling of amine (XIII) with lactone (VII) in refluxing isopropanol produced amide (XIV). The title compound was then obtained by acidic hydrolysis of the remaining acetonide function of (XIV).

参考文献中间体

合成目标

【1】 Kinder, F.R. Jr.; Versace, R.W.; Bair, K.W.; et al.; Synthesis and antitumor activity of ester-modified analogues of bengamide B. J Med Chem 2001, 44, 22, 3692.
【2】 Bair, K.W.; Kinder, F.R. Jr.; Jagoe, C.T. (Novartis AG); Certain substd. caprolactams, pharmaceutical compsns. containing them and their use in treating tumors. EP 1131297; WO 0029382 .
【3】 Bair, K.W.; Wattanasin, S.; Versace, R.W.; Kinder, F.R. Jr.; Jagoe, C.T. (Novartis AG); Certain substd. caprolactams, pharmaceutical compsns. containing them and a process for their preparation. US 6239127 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	54665	(4R,4aR,7R,7aS)-4-[(E)-3,3-dimethyl-1-butenyl]-7-methoxy-2,2-dimethyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one		C₁₅H₂₄O₅	详情	详情
(VIII)	47774	(2S,5R)-2,6-diamino-5-hydroxyhexanoic acid		C₆H₁₄N₂O₃	详情	详情
(IX)	47775	(3S,6R)-3-amino-6-hydroxy-2-azepanone		C₆H₁₂N₂O₂	详情	详情
(X)	47776	tert-butyl (3S,6R)-6-hydroxy-2-oxoazepanylcarbamate		C₁₁H₂₀N₂O₄	详情	详情
(XI)	17220	cyclohexanecarbonyl chloride; Cyclohexanecarboxylic acid chloride	2719-27-9	C₇H₁₁ClO	详情	详情
(XII)	54666	(3R,6S)-6-[(tert-butoxycarbonyl)amino]-7-oxoazepanyl cyclohexanecarboxylate		C₁₈H₃₀N₂O₅	详情	详情
(XIII)	54667	(3R,6S)-6-amino-7-oxoazepanyl cyclohexanecarboxylate		C₁₃H₂₂N₂O₃	详情	详情
(XIV)	54668	(3R,6S)-6-[((2R)-2-{(4R,5R,6R)-6-[(E)-3,3-dimethyl-1-butenyl]-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl}-2-methoxyethanoyl)amino]-7-oxoazepanyl cyclohexanecarboxylate		C₂₈H₄₆N₂O₈	详情	详情

Extended Information