N-(5-bromopentanoyl)methanesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】39702

【品名】N-(5-bromopentanoyl)methanesulfonamide

【CA登记号】

【分子式】C₆H₁₂BrNO₃S

【分子量】258.13622

【元素组成】C 27.92% H 4.69% Br 30.95% N 5.43% O 18.59% S 12.42%

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：(XIII)

A Wittig condensation of [4-(methanesulfonylaminocarbonyl)butyl]triphenylphosphonium bromide (X) [the phosphonium bromide (X) is prepared bv reaction of 5-bromovaleryl chloride (Xl) with methanesulfonamide (XII) at 100 C to give N-methanesulfonyl-5-bromovaleramide (XIII), which is then condensed with triphenylphosphine in refluxing acetonitrile] with hemiacetal (IX) by means of Na in DMSO affords N-methanesulfonyl-9alpha-hydroxy-11alpha,15alpha-bis(tetrahydropyranyloxy)-16-phenoxy-5-cis-13-trans-omega-tetranorprostadienamide (XIV), which is then oxidized with the Jones reagent in acetone to the keto compound (XV). Finally, this compound is deprotected with acetic acid.

参考文献中间体

合成目标

【1】 Castaner, J.; Wescott, A.L.; Sulprostone. Drugs Fut 1978, 3, 1, 59.
【2】 Beil, W.; Hoeppener, A.; Wolff, H.J.; Beil, H.; Substituted 16,17,18,19,20-pentanorprostaglandins. DE 2355540; ES 433046; ES 433047; FR 2205335; GB 1456512; JP 49093342; JP 52053841 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	32047	(3aR,4S,5R,6aS)-4-[(E,3R)-4-phenoxy-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-butenyl]-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-ol		C₂₉H₄₂O₇	详情	详情
(X)	39699	[5-[(methylsulfonyl)amino]-5-oxopentyl](triphenyl)phosphonium bromide		C₂₄H₂₇BrNO₃PS	详情	详情
(XI)	39700	5-bromopentanoyl chloride	4509-90-4	C₅H₈BrClO	详情	详情
(XII)	39701	methanesulfonamide	3144-09-0	CH₅NO₂S	详情	详情
(XIII)	39702	N-(5-bromopentanoyl)methanesulfonamide		C₆H₁₂BrNO₃S	详情	详情
(XIV)	39703	N-((Z)-7-[(1R,2S,3R,5S)-5-hydroxy-2-[(E,3R)-4-phenoxy-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-butenyl]-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoyl)methanesulfonamide		C₃₅H₅₃NO₉S	详情	详情
(XV)	39704	N-((Z)-7-[(1R,2S,3R)-2-[(E,3R)-3-hydroxy-4-phenoxy-1-butenyl]-5-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoyl)methanesulfonamide		C₂₉H₄₁NO₈S	详情	详情

Extended Information