3-methyl-3-[(methylsulfonyl)amino]-N-[(3R)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]butanamide -Drug Synthesis Database

【结构式】

【分子编号】15930

【品名】3-methyl-3-[(methylsulfonyl)amino]-N-[(3R)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]butanamide

【CA登记号】

【分子式】C₁₆H₂₃N₃O₄S

【分子量】353.44244

【元素组成】C 54.37% H 6.56% N 11.89% O 18.11% S 9.07%

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：(V)

A synthesis of L-692429 has been reported: The cyclization of isobutene (I) with chlorosulfonyl isocyanate (II) gives 1-(chlorosulfonyl)-4,4-dimethylazetidin-2-one (III), which is condensed with 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (IV) by means of triethylamine in methanol to yield 3-methyl-3-(methylsulfonamido)-N-[2-oxo-2,3,4,5-tetrahydro-1H-1-benzaze pin-3(R)-yl]butyramide (V). The reaction of (V) with 2'-[1-(triphenylmethyl)tetrazol-5-yl]biphenyl-4-ylmethyl bromide (VI) by means of NaH in THF/DMF affords protected L-692429, which is finally deprotected by a treatment with 5N HCl.

参考文献中间体

合成目标

【1】 Bergan, J.J.; Reider, P.J.; McNamara, J.M.; Volante, R.P.; Bhupathy, M.; A convergent synthesis of a novel non-peptidyl growth hormone secretagogue, L-692,429. Tetrahedron Lett 1995, 36, 52, 9445.
【2】 Schoen, W.R.; et al.; A novel 3-substituted benzazepinone growth hormone secretagogue (L-692,429). J Med Chem 1994, 37, 7, 897.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	15926	2-methyl-1-propene; isobutylene	115-11-7	C₄H₈	详情	详情
(II)	14101	Chlorosulfonyl isocyanate	1189-71-5	CClNO₃S	详情	详情
(III)	15928	2,2-dimethyl-4-oxo-1-azetanesulfonyl chloride		C₅H₈ClNO₃S	详情	详情
(IV)	15929	(3R)-3-amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one		C₁₀H₁₂N₂O	详情	详情
(V)	15930	3-methyl-3-[(methylsulfonyl)amino]-N-[(3R)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]butanamide		C₁₆H₂₃N₃O₄S	详情	详情
(VI)	15538	5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-trityl-2H-1,2,3,4-tetraazole	124750-51-2	C₃₃H₂₅BrN₄	详情	详情
(VII)	15932	3-methyl-3-[(methylsulfonyl)amino]-N-((3R)-2-oxo-1-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)butanamide		C₄₉H₄₇N₇O₄S	详情	详情

Extended Information