(2S)-2-ethoxy-N-[(1S)-2-hydroxy-1-phenylethyl]-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]propanamide -Drug Synthesis Database

【结构式】

【分子编号】51692

【品名】(2S)-2-ethoxy-N-[(1S)-2-hydroxy-1-phenylethyl]-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]propanamide

【CA登记号】

【分子式】C₃₃H₃₄N₂O₅

【分子量】538.64344

【元素组成】C 73.59% H 6.36% N 5.2% O 14.85%

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：(XX)

Resolution of the racemic acid (X) was carried out via activation as the mixed anhydride (XVIII) upon treatment with pivaloyl chloride (XVII) and triethylamine. Anhydride (XVIII) was then condensed with (S)-2-phenylglycinol (XIX), producing a separable mixture of diastereomeric amides. Isolation of the desired (S,S)-isomer (XX) by silica gel chromatography, followed by amide hydrolysis under acidic conditions, furnished the target (S)-enantiomer.

参考文献中间体

合成目标

【2】 Kalchar, S.; Lohray, V.B.; Lohray, B.B.; Chakrabarti, R.; Bajji, A.C.; Ramanujam, R. (Dr. Reddy's Research Foundation); Novel tricyclic cpds. and their use in medicine; process for their preparation and pharmaceutical compsns. containing them. EP 1049684; JP 2001519422; WO 9919313 .
【3】 Rajagopalan, R.; Ashok, C.B.; Shivaramayya, K.; Gurram, R.M.; Lohray, B.B.; Paraselli, B.R.; Rajan, C.; Lohray, V.B. (Dr. Reddy's Research Foundation); Novel tricyclic cpds. and their use in medicine; process for their preparation and pharmaceutical compsn. containing them. EP 1155006; WO 0050414 .
【1】 Lohray, B.B.; et al.; (-)-3-[4-[2-(Phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoic acid[(-)DRF 2725]: A dual PPAR agonist with potent antihyperglycemic and lipid modulating activity. J Med Chem 2001, 44, 16, 2675.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	51681	2-ethoxy-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]propionic acid		C₂₅H₂₅NO₅	详情	详情
(XVII)	13597	2,2-Dimethylpropanoyl chloride; Pivaloyl chloride	3282-30-2	C₅H₉ClO	详情	详情
(XVIII)	51691	1,1-dimethylpropionic 1-ethoxy-2-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]propionic anhydride		C₃₀H₃₃NO₆	详情	详情
(XIX)	10973	(2S)-2-Amino-2-phenyl-1-ethanol; (S)-2-Hydroxy-1-phenylethylamine; (S)-(+)-2-Phenylglycinol; (S)-2-Amino-2-phenyl-1-ethanol	20989-17-7	C₈H₁₁NO	详情	详情
(XX)	51692	(2S)-2-ethoxy-N-[(1S)-2-hydroxy-1-phenylethyl]-3-[4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl]propanamide		C₃₃H₃₄N₂O₅	详情	详情

Extended Information