2-[(3S)-3-([2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoyl]amino)-3-methyl-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]acetic acid -Drug Synthesis Database

【结构式】

【分子编号】41691

【品名】2-[(3S)-3-([2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoyl]amino)-3-methyl-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]acetic acid

【CA登记号】

【分子式】C₂₀H₂₉N₃O₆S

【分子量】439.53288

【元素组成】C 54.65% H 6.65% N 9.56% O 21.84% S 7.3%

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：(XVIII)

Synthesis of EN 290154: Cleavage of both the Fmoc protecting group and ethyl ester of (XV) by means of HBr in HOAc followed by Boc protection affords (XVI) which is then anchored to a chloromethylated resin to yield (XVII). Deprotection of dihydro-benzothiazepinone (XVII) with TFA in presence of ethanedithiol, followed by coupling with Boc-Ser-OH by means of BOP/DIEA in CH2Cl2, yields derivative (XVIII). Deprotection of (XVIIII) followed by coupling with intermediate (XIV) in the same conditions described for (XVII) affords derivative (XIX). Next steps include sequencial Boc removal and coupling with Boc-Arg(Tos)-OH and then Boc-Lys(Fmoc)-OH. Finally the product is cleaved from the resin by means of HF/anisole.

参考文献中间体

合成目标

【1】 Bedos, P.; Daffix, I.; Amblard, M.; et al.; Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety. J Med Chem 1999, 42, 20, 4185.
【2】 Amblard, M.; Subra, G.; Bedos, P.; et al.; A rational approach to the design and synthesis of a new bradykinin B1 receptor antagonist. J Med Chem 2000, 43, 12, 2387.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVI),(XVII)	41690	2-[(3S)-3-[(tert-butoxycarbonyl)amino]-3-methyl-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]acetic acid	C₁₇H₂₄N₂O₄S	详情	详情
(XIV)	41688	2-[8-(tert-butoxycarbonyl)-4-oxo-1-phenethyl-1,3,8-triazaspiro[4.5]dec-3-yl]acetic acid	C₂₂H₃₁N₃O₅	详情	详情
(XV)	41689	ethyl 2-[(3S)-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methyl-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]acetate	C₂₉H₃₀N₂O₄S	详情	详情
(XVIII)	41691	2-[(3S)-3-([2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoyl]amino)-3-methyl-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]acetic acid	C₂₀H₂₉N₃O₆S	详情	详情
(XIX)	41692	2-[(3S)-3-[[2-([2-[8-(tert-butoxycarbonyl)-4-oxo-1-phenethyl-1,3,8-triazaspiro[4.5]dec-3-yl]acetyl]amino)-3-hydroxypropanoyl]amino]-3-methyl-3,4-dihydro-1,5-benzothiazepin-5(2H)-yl]acetic acid	C₃₇H₅₀N₆O₈S	详情	详情

Extended Information