(4S)-4-benzyl-3-[(2R)-2-propyl-4-hexynoyl]-1,3-oxazolidin-2-one -Drug Synthesis Database

【结构式】

【分子编号】29432

【品名】(4S)-4-benzyl-3-[(2R)-2-propyl-4-hexynoyl]-1,3-oxazolidin-2-one

【CA登记号】

【分子式】C₁₉H₂₃NO₃

【分子量】313.39656

【元素组成】C 72.82% H 7.4% N 4.47% O 15.32%

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)

Condensation of pentanoyl chloride (I) with (S)-4-benzyl-2-oxazolidinone (II) in the presence of n-butyllithium afforded the chiral N-acyl oxazolidinone (III). Subsequent asymetric alkylation of (III) with 1-bromo-2-butyne (IV) using LDA as the base produced the alkylated diastereoisomer (V). The chiral auxiliary oxazolidinone was finally removed by hydrolysis with lithium hydroperoxide to afford the required (R)-carboxylic acid.

参考文献中间体

合成目标

【1】 Hauck, R.-S.; Elmazar, M.M.E.; Nau, H.; Bojic, U.; VPA-analogous antiepileptics. DE 4231085; US 5786380; WO 9406743 .

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)	15116	pentanoyl chloride; valeryl chloride	638-29-9	C₅H₉ClO	详情	详情
(II)	14694	(S)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-1,3-oxazolan-2-one; (S)-(-)-4-Benzyl-2-oxazolidinone	90719-32-7	C₁₀H₁₁NO₂	详情	详情
(III)	29431	(4S)-4-benzyl-3-pentanoyl-1,3-oxazolidin-2-one		C₁₅H₁₉NO₃	详情	详情
(IV)	29428	1-bromo-2-butyne	3355-28-0	C₄H₅Br	详情	详情
(V)	29432	(4S)-4-benzyl-3-[(2R)-2-propyl-4-hexynoyl]-1,3-oxazolidin-2-one		C₁₉H₂₃NO₃	详情	详情

Extended Information