Hydrochloric Acid → 4-(2-Hydroxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester

関与物質

役割	名称	HCID	仕込み量
反応物	Hydrochloric Acid	HCID 313	—
反応物	3-Methylsalicylic Acid	HCID 6738	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
反応物	Methyl 4-aminothiane-4-carboxylate	HCID 15524434	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	4-(2-Hydroxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester	HCID 59314262	13.2%

反応手順

To a solution of HCl salt of 4-amino-tetrahydro-thiopyran-4-carboxylic acid methyl ester (529 mg, 2.5 mmol), 2-hydroxy-3-methyl-benzoic acid (380 mg, 2.5 mmol), HATU (1.14 g, 3.0 mmol) in anhydrous DMF (20 mL) is added DIPEA (1.66 mL, 10 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (30 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 10-80% EtOAc in heptane) to give a pure product (27) as white solid (102 mg, 13%).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08569535B2
出典データセット	uspto-grants-2013_10
ORD ID	ord-fb5b094bc0f940f4bcca61c454ca535d
出典メモ	uspto-grants-2013_10