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【结 构 式】

【分子编号】25554

【品名】methyl (2R)-2-hydroxy-2-phenylethanoate

【CA登记号】20698-91-3

【 分 子 式 】C9H10O3

【 分 子 量 】166.1766

【元素组成】C 65.05% H 6.07% O 28.88%

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:(VII)

Condensation of halo ester (I) with 2-mercaptopropionic acid (II) provided thioether (III). After conversion of the carboxylic acid group of (III) into acid chloride (IV), Friedel-Crafts cyclization yielded the racemic trans benzothiepinone (V). Subsequent ester hydrolysis gave carboxylic acid (VI). The required (2R,4S) enantiomer (IX) was then isolated by condensation with methyl (R)-mandelate (VII), followed by recrystallization of the diastereoisomeric ester (VIII) from ethyl acetate-hexane, and further hydrolysis with HCl in AcOH. Finally, coupling of (IX) with diethyl 4-aminobenzylphosphonate (X) by means of EDC and HOBt furnished the title compound.

1 Oda, T.; et al.; Synthesis of novel 2-benzothiopyran and 3-benzothiepin derivatives and their stimulatory effect on bone formation. Symp Med Chem 1998, Abst 2-P-31.
2 Sohda, T.; Taketomi, S.; Oda, T. (Takeda Chemical Industries, Ltd.); Optically active benzothiepine deriv., its preparation and use. CA 2166152; EP 0719782; JP 1996231569; JP 1997183784 .
3 Hoshino, T.; Muranishi, H.; Taketomi, S.; Iwasa, S. (Takeda Chemical Industries, Ltd.); Osteogenetic promoting pharmaceutical compsn.. JP 1997263545; WO 9639134 .
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) 25550 ethyl 3-(1,3-benzodioxol-5-yl)-2-bromopropanoate C12H13BrO4 详情 详情
(II) 24361 2-sulfanylpropionic acid; 2-mercaptopropionic acid 57965-30-7 C3H6O2S 详情 详情
(III) 25552 2-[[1-(1,3-benzodioxol-5-ylmethyl)-2-ethoxy-2-oxoethyl]sulfanyl]propionic acid C15H18O6S 详情 详情
(IV) 25551 ethyl 3-(1,3-benzodioxol-5-yl)-2-[(2-chloro-1-methyl-2-oxoethyl)sulfanyl]propanoate C15H17ClO5S 详情 详情
(V) 25553 ethyl (6R,8S)-8-methyl-9-oxo-5,6,8,9-tetrahydrothiepino[4,5-f][1,3]benzodioxole-6-carboxylate C15H16O5S 详情 详情
(VI) 24367 8(S)-Methyl-9-oxo-5,6,8,9-tetrahydro-1,3-dioxolo[4,5-h][3]benzothiepine-6(R)-carboxylic acid C13H12O5S 详情 详情
(VII) 25554 methyl (2R)-2-hydroxy-2-phenylethanoate 20698-91-3 C9H10O3 详情 详情
(VIII) 24366 8(S)-Methyl-9-oxo-5,6,8,9-tetrahydro-1,3-dioxolo[4,5-h][3]benzothiepine-6(R)-carboxylic acid 1(R)-(methoxycarbonyl)-1-benzyl ester C22H20O7S 详情 详情
(IX) 24367 8(S)-Methyl-9-oxo-5,6,8,9-tetrahydro-1,3-dioxolo[4,5-h][3]benzothiepine-6(R)-carboxylic acid C13H12O5S 详情 详情
(X) 24368 4-Aminobenzylphosphonic acid diethyl ester 20074-79-7 C11H18NO3P 详情 详情
Extended Information