ABS-103R, R-ABS-103, R-103, -Drug Synthesis Database

【结构式】

【药物名称】ABS-103R, R-ABS-103, R-103

【化学名称】2(R)-Propyl-4-hexynoic acid

【CA登记号】155899-34-6

【分子式】C₉H₁₄O₂

【分子量】154.21073

【开发单位】American Biogenetic Sciences (Originator)

【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS

合成路线1

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

【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

Drug NewChemical Entity Original Patent(1)