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0 °C

tert-butyl [2-{[4-(aminomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate (2.0 g, 4.72 mmol) was suspended in dichloromethane (50 ml). Hunig's Base (1 ml, 5.73 mmol) was added. The solution was cooled to 0° C. Chlorocarbonic acid chloromethyl ester (0.5 ml, 5.68 mmol) was added slowly. The reaction was stirred for approximately 1-2 h. The mixture, while cold, was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate. The aqueous layer was extracted three times with dichloromethane. The combined organic layers were dried over Na2SO4, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with EtOAc/hexane. MS: calc'd 417 (MH+-Boc), exp 417 (MH+-Boc).

1. washwashed with saturated aqueous sodium bicarbonate
2. extractionThe aqueous layer was extracted three times with dichloromethane
3. dry with materialThe combined organic layers were dried over Na2SO4
4. filtrationfiltered
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel eluting with EtOAc/hexane