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【结 构 式】

【分子编号】51080

【品名】butyl 2-(4-[[(2R)-3-chloro-2-hydroxypropyl]oxy]phenyl)acetate

【CA登记号】

【 分 子 式 】C15H21ClO4

【 分 子 量 】300.78204

【元素组成】C 59.9% H 7.04% Cl 11.79% O 21.28%

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:(S)-(IX)

Esterification of p-hydroxyphenylacetic acid (I) with NaHSO4 in refluxing butanol provides butyl acetate derivative (II), which is then subjected to reaction with epichlorohydrin (III) in pyridine to furnish a mixture of epoxypropane (IV) and chloro derivative (V). Treatment of the mixture (IV)/(V) with HCl affords derivative (VI), which is then selectively acylated by means of Lipase Amano PS (LAPS) and vinyl acetate or acetic anhydride/diisopropyl ether to yield compound (S)-(VII). Treatment of the mixture (IV)/(V) with acetyl chloride gives derivative (VIII), which is selectively deacylated using LAPS in butanol/diisopropyl ether to afford derivative (S)-(IX). Coupling of derivative (S)-(VII) with isopropylamine (X) in H2O, followed by removal of the acetyl group with NaOH furnishes derivative (XI) (alternatively, (XI) can also be synthesized by coupling of (S)-(IX) with amine (X)). Finally, conversion of (XI) into the desired product is achieved by treatment with ammonium hydroxide in MeOH.

1 Banerji, A.A.; Bevinakatti, H.S.; Lipase catalysis in organic solvents. Application to the synthesis of (R)- and (S)-atenolol. J Org Chem 1992, 57, 22, 6003.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V),(VI) 51078 butyl 2-[4-(3-chloro-2-hydroxypropoxy)phenyl]acetate C15H21ClO4 详情 详情
(S)-(VII) 51079 butyl 2-(4-[[(2R)-2-(acetoxy)-3-chloropropyl]oxy]phenyl)acetate C17H23ClO5 详情 详情
(S)-(IX) 51080 butyl 2-(4-[[(2R)-3-chloro-2-hydroxypropyl]oxy]phenyl)acetate C15H21ClO4 详情 详情
(I) 18430 2-(4-Hydroxyphenyl)acetic acid; 4-Hydroxyphenylacetic acid 156-38-7 C8H8O3 详情 详情
(II) 51075 butyl 2-(4-hydroxyphenyl)acetate C12H16O3 详情 详情
(III) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(IV) 51077 butyl 2-[4-(2-oxiranylmethoxy)phenyl]acetate C15H20O4 详情 详情
(VIII) 51082 butyl 2-[4-[2-(acetoxy)-3-chloropropoxy]phenyl]acetate C17H23ClO5 详情 详情
(X) 23933 2-Propanamine; Isopropylamine 75-31-0 C3H9N 详情 详情
(XI) 51081 butyl 2-(4-[[(2S)-2-hydroxy-3-(isopropylamino)propyl]oxy]phenyl)acetate C18H29NO4 详情 详情
Extended Information