2-Aminopropanol → N-(2-hydroxy-1-methyl-ethyl)-3-iodobenzamide

To a solution of 3-iodobenzoic acid (10.02 g, 40.30 mmol), in dry dichloromethane, at room temperature (180 mL) under a nitrogen atmosphere, EDCI (7.72 g, 40.30 mmol) was added followed by triethylamine (8.0 mL, 60.45 mmol) and the mixture was stirred at room temperature for further 5 minutes. DL Alaninol (3.02 g, 40.3 mmol) was then added and the mixture stirred at room temperature for 16 hrs. The reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL) followed by saturated brine solution (100 mL). The organics were separated and dried over magnesium sulfate and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica gel (DCM:MeOH, 1% to 8% methanol gradient) to afford compound 1 (4.14 g, 13.6 mmol, 34% yield) as an off white solid.

1. stirringthe mixture stirred at room temperature for 16 hrs
2. washThe reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL)
3. customThe organics were separated
4. dry with materialdried over magnesium sulfate
5. customthe solvent evaporated under vacuum
6. customThe residue was purified by flash column chromatography on silica gel (DCM:MeOH, 1% to 8% methanol gradient)

ORDレコード

ord-c4a65e7e43f94ca0b5a432db548271d9

出典データセット

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07696382B2