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【结 构 式】

【分子编号】35063

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

【CA登记号】

【 分 子 式 】C18H25NO3

【 分 子 量 】303.40144

【元素组成】C 71.26% H 8.31% N 4.62% O 15.82%

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:(VI)

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
Extended Information