Trifluoroacetic acid → HCID 53857452, compound

Trifluoroacetic acid (10 ml) was added to a solution of the title compound of Example 10 (3.6 g, 0.0136 mole) in methylene chloride (5 ml) with stirring. After several minutes, methyl thioglycolate (1.59 g, 0.015 mole) was added, and the reaction mixture was stirred for 30 minutes. The reaction mixture was poured into methanol (50 ml) containing lithium hydroxide hydrate (12.6 g, 0.30 mole). Water (125 ml) was slowly added to the mixture, and then the mixture was extracted with diethyl ether (100 ml). The aqueous phase was acidified with concentrated hydrochloric acid and extracted twice with 100 ml of diethyl ether. The combined diethyl ether extracts were washed with water (30 ml), 5% sodium bicarbonate (50 ml) and brine (50 ml), dried over anhydrous magnesium sulfate, filtered and concentrated with a rotary evaporator to give the crude product as an oil. The product was purified by silica gel chromatography. The structure was supported by NMR, infrared spectroscopy, and elemental analysis.

1. waitAfter several minutes
2. stirringthe reaction mixture was stirred for 30 minutes
3. extractionthe mixture was extracted with diethyl ether (100 ml)
4. extractionextracted twice with 100 ml of diethyl ether
5. washThe combined diethyl ether extracts were washed with water (30 ml), 5% sodium bicarbonate (50 ml) and brine (50 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated with a rotary evaporator

ORD record

ord-70ee95d7dbde4dd689d047f7572476da

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05476944