Trifluoroacetic acid → HCID 69621723, compound

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Reaction Steps

The compound from above, [1-(2-benzyloxy-1-{[5-(4-chloro-phenyl)-3,3-dimethyl-1,1-dioxo-2,3-dihydro-1H-1λ6-isothiazol-4-ylmethyl]-ethyl-carbamoyl}-ethylcarbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (1.00 g, 1.48 mmol) was dissolved in dichloromethane (30 mL) and trifluoroacetic acid added (5 mL) and the mixture stirred for 2 hours at room temperature. The mixture was concentrated in vacuo and the residue treated with saturated aqueous sodium bicarbonate followed by extraction with ethyl acetate. The combined extracts were dried over sodium sulfate. Concentration left a residue which was chromatographed over silica (methanol/chloroform) to give the amine. This amine was dissolved in minimal ethyl acetate and treated with excess ether/hydrochloric acid. Concentration and drying netted 0.37 g (41%) of the desired hydrochloride salt as a white solid. Anal. Calc'd for C28H3ClN4O5S.1.1HCl: C, 54.49; H, 6.22; N, 9.38. Found: C, 54.17; H, 6.16; N, 9.38. m.p. 107–113° C. MS(ES): (M+1)+ 579.4 m/z.

Provenance & Evidence