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【结 构 式】

【分子编号】60620

【品名】3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl chloride

【CA登记号】

【 分 子 式 】C4H4ClF3O2

【 分 子 量 】176.5224696

【元素组成】C 27.22% H 2.28% Cl 20.08% F 32.29% O 18.13%

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:(X)

Alkylation of 3-aminothiophenol (II) with methyl 3-(bromomethyl)thiophene-2-carboxylate (I) provides thioether (III). After protection of the amino group of (III) as the corresponding acetamide (IV), its methyl ester group is hydrolyzed under alkaline conditions, to provide the carboxylic acid (V). Activation of acid (V) with trifluoroacetic anhydride, followed by cyclization in the presence of boron trifluoride etherate gives rise to a mixture of regioisomeric thienobenzothiepinones (VI) and (VII), which are separated by column chromatography. Acidic hydrolysis of the desired isomer (VII) provides amine (VIII). Acid chloride (X), prepared by chlorination of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (IX), is then condensed with amine (VIII) to furnish amide (XI). Finally, oxidation of the sulfide group of (XI) to the title sulfone is accomplished by treatment with m-chloroperbenzoic acid

1 Mimura, T.; Ogasa, T.; Mori, S.; Matsushita, T.; Imai, E. (Kyowa Hakko Kogyo Co., Ltd.); Preparation method of tricyclic cpds.. JP 2002053580 .
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) 60612 methyl 3-(bromomethyl)-2-thiophenecarboxylate C7H7BrO2S 详情 详情
(II) 60613 3-aminobenzenethiol; 3-aminophenylhydrosulfide C6H7NS 详情 详情
(III) 60614 methyl 3-{[(3-aminophenyl)sulfanyl]methyl}-2-thiophenecarboxylate C13H13NO2S2 详情 详情
(IV) 60615 methyl 3-({[3-(acetylamino)phenyl]sulfanyl}methyl)-2-thiophenecarboxylate C15H15NO3S2 详情 详情
(V) 60616 3-({[3-(acetylamino)phenyl]sulfanyl}methyl)-2-thiophenecarboxylic acid C14H13NO3S2 详情 详情
(VI) 60617 N-(10-oxo-4,10-dihydrothieno[3,2-c][1]benzothiepin-7-yl)acetamide C14H11NO2S2 详情 详情
(VII) 60618 N-(10-oxo-4,10-dihydrothieno[3,2-c][1]benzothiepin-9-yl)acetamide C14H11NO2S2 详情 详情
(VIII) 60619 9-aminothieno[3,2-c][1]benzothiepin-10(4H)-one C12H9NOS2 详情 详情
(IX) 34552 trimethylsilyl (2R)-3,3,3-trifluoro-2-methyl-2-[(trimethylsilyl)oxy]propanoate C10H21F3O3Si2 详情 详情
(X) 60620 3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl chloride C4H4ClF3O2 详情 详情
(XI) 60621 3,3,3-trifluoro-2-hydroxy-2-methyl-N-(10-oxo-4,10-dihydrothieno[3,2-c][1]benzothiepin-9-yl)propanamide C16H12F3NO3S2 详情 详情
Extended Information