【结 构 式】 |
【药物名称】(R)-PID 【化学名称】2(R)-Isopropylpentanamide 【CA登记号】6098-19-7 (racemate) 【 分 子 式 】C8H17NO 【 分 子 量 】143.23079 |
【开发单位】Hebrew University (Originator) 【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS |
合成路线1
Treatment of S-4-benzyl-2-oxazolidinone (II) with n-butyllithium, followed by acylation with valeroyl chloride (I) afforded the N-valeroyloxazolidinone (III). Subsequent alkylation of (III) with isopropyl triflate (V), prepared from isopropyl alcohol (IV) and trifluoromethanesulfonic anhydride, in the presence of LDA produced the (4S,2'R)-2-isopropylvaleroyl derivative (VI). Hydrolysis of (VI) using lithium peroxide yielded the chiral carboxylic acid (VII), which was converted to the corresponding acid chloride (VIII) by treatment with oxalyl chloride. Finally, reaction of (VIII) with ammonia furnished the title amide.
【1】 Yagen, B.; Bialer, M.; Spigelstein, O. (Yissum Research Development Co.); Propylisopropyl acetic acid and propylisopropyl acetamide stereoisomers, a method for their synthesis and pharmaceutical compsns. containing them. WO 9954282 . |
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) | 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 |
(II) | 15116 | pentanoyl chloride; valeryl chloride | 638-29-9 | C5H9ClO | 详情 | 详情 |
(III) | 29431 | (4S)-4-benzyl-3-pentanoyl-1,3-oxazolidin-2-one | C15H19NO3 | 详情 | 详情 | |
(IV) | 19250 | 2-propanol | 67-63-0 | C3H8O | 详情 | 详情 |
(V) | 35062 | isopropyl trifluoromethanesulfonate | C4H7F3O3S | 详情 | 详情 | |
(VI) | 35063 | (4S)-4-benzyl-3-[(2R)-2-isopropylpentanoyl]-1,3-oxazolidin-2-one | C18H25NO3 | 详情 | 详情 | |
(VII) | 35064 | (2R)-2-isopropylpentanoic acid | C8H16O2 | 详情 | 详情 | |
(VIII) | 35065 | (2R)-2-isopropylpentanoyl chloride | C8H15ClO | 详情 | 详情 |