Trifluoroacetic acid → HCID 86704329, compound

To a solution of N-iodosuccinamide (8.3 g, 37 mmol) in 80 mL of dry acetonitrile were added (S)-3-(3,4-dimethoxyphenyl)1-methoxy-1-oxopropan-2-amine hydrochloride (4.63 g, 16.8 mmol) and trifluoroacetic acid (2.7 mL, 37 mmol) with stirring. The reaction mixture was stirred at room temperature in a 250 mL round bottom flask protected from light for 2 and half hours. The acetonitrile was removed and the remaining solid was taken up into water. The water solution was treated with saturated sodium bisulfite aqueous solution until the purple color disappeared. The pH was adjusted to 8 using saturated sodium bicarbonate solution. The neutralized aqueous solution was extracted with dichloromethane (3×50 mL) The organic layers were combined and dried over sodium sulfate. The solvent was evaporated to yield (S)-3-(2-Iodo-4,5-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-amine (5.17 g, 98%) as a pale yellow oil. The crude product was dried over dynamic vacuum overnight and was sufficiently pure for subsequent steps.

1. stirringThe reaction mixture was stirred at room temperature in a 250 mL round bottom flask
2. customThe acetonitrile was removed
3. additionThe water solution was treated with saturated sodium bisulfite aqueous solution until the purple color
4. extractionThe neutralized aqueous solution was extracted with dichloromethane (3×50 mL) The organic layers
5. dry with materialdried over sodium sulfate
6. customThe solvent was evaporated

ORD record

ord-52e46da7d04f464d92b95f475bbc167e

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278959B2