(2S)-2-sulfanyl-1-propanol -Drug Synthesis Database

【结构式】

【分子编号】35743

【品名】(2S)-2-sulfanyl-1-propanol

【CA登记号】

【分子式】C₃H₈OS

【分子量】92.16192

【元素组成】C 39.1% H 8.75% O 17.36% S 34.79%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

Methyl (S)-lactate (I) was converted to chloride (II) by treatment with SOCl2. Subsequent displacement in (II) by cesium thioacetate produced thioester (III). Reduction of the ester group of (III) with concomitant thioester cleavage by means of LiAlH4 in cold THF furnished mercaptoalcohol (IV).

参考文献中间体

合成目标

【1】 Friesen, R.W.; Deschênes, D.; Gordon, R.; Brideau, C.; Riendau, D.; Savoie, C.; Dubé, D.; Girard, Y.; Fortin, R.; Chan, C.-C.; 2-Heterosubstituted-3-(4-methylsulfonyl)phenyl-5-trifluromethyl pyridines as selective and orally active cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett 1999, 9, 12, 1715.

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)	17075	propionic acid, 2-hydroxy-, methyl ester, (S)-; methyl (2S)-2-hydroxypropanoate	27871-49-4	C₄H₈O₃	详情	详情
(II)	35742	methyl (2S)-2-chloropropanoate		C₄H₇ClO₂	详情	详情
(III)	16680	methyl (2S)-2-(acetylsulfanyl)propanoate		C₆H₁₀O₃S	详情	详情
(IV)	35743	(2S)-2-sulfanyl-1-propanol		C₃H₈OS	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Bromination of 2-amino-5-trifluoromethylpyridine (V) in AcOH provided bromopyridine (VI), which was submitted to a Suzuki coupling with 4-(methylthio)benzeneboronic acid (VII) yielding the phenylpyridine derivative (VIII). Oxidation of the methylthio group of (VIII) to the corresponding sulfone (IX) was carried out by treatment with N-methylmorpholine-N-oxide in the presence of OsO4. Diazotization of the amino group of (IX) generated the pyridone (X), and further chlorination employing POCl3 provided chloropyridine (XI). Finally, condensation of (XI) with (S)-2-mercaptopropanol (IV) yielded the title compound.

参考文献中间体

合成目标

【1】 Friesen, R.W.; Deschênes, D.; Gordon, R.; Brideau, C.; Riendau, D.; Savoie, C.; Dubé, D.; Girard, Y.; Fortin, R.; Chan, C.-C.; 2-Heterosubstituted-3-(4-methylsulfonyl)phenyl-5-trifluromethyl pyridines as selective and orally active cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett 1999, 9, 12, 1715.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	35743	(2S)-2-sulfanyl-1-propanol		C₃H₈OS	详情	详情
(V)	35744	5-(trifluoromethyl)-2-pyridinylamine; 5-(trifluoromethyl)-2-pyridinamine	74784-70-6	C₆H₅F₃N₂	详情	详情
(VI)	35745	3-bromo-5-(trifluoromethyl)-2-pyridinamine; 3-bromo-5-(trifluoromethyl)-2-pyridinylamine		C₆H₄BrF₃N₂	详情	详情
(VII)	18561	4-(methylsulfanyl)phenylboronic acid	98546-51-1	C₇H₉BO₂S	详情	详情
(VIII)	35746	3-[4-(methylsulfanyl)phenyl]-5-(trifluoromethyl)-2-pyridinamine; 3-[4-(methylsulfanyl)phenyl]-5-(trifluoromethyl)-2-pyridinylamine		C₁₃H₁₁F₃N₂S	详情	详情
(IX)	35747	3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-2-pyridinylamine; 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-2-pyridinamine		C₁₃H₁₁F₃N₂O₂S	详情	详情
(X)	35748	3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-2(1H)-pyridinone		C₁₃H₁₀F₃NO₃S	详情	详情
(XI)	35749	2-chloro-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)pyridine; 4-[2-chloro-5-(trifluoromethyl)-3-pyridinyl]phenyl methyl sulfone		C₁₃H₉ClF₃NO₂S	详情	详情

Extended Information