tert-butyl N-(2-anilino-2-oxoethyl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40 ml of dichloromethane and 20 ml of trifluoroacetic acid were added to 687 mg (2.74 mmol) of t-butyl phenylcarbamoylmethylcarbamate, and they were stirred at room temperature for 3 hours. Dichloromethane and trifluoroacetic acid were evaporated under reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue. After the extraction with ethyl acetate and then with dichloromethane, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound. Dichloromethane and trifluoroacetic acid were evaporated under reduced pressure A saturated aqueous sodium hydrogencarbonate solution was added to the residue After the extraction with ethyl acetate with dichloromethane, the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.27 g (1.19 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 681 mg (5.04 mmol) of 1-hydroxybenzotriazole and 0.95 ml (6.82 mmol) of triethylamine were added to 1.15 g (6.56 mmol) of t-butoxycarbonylglycine in 20 ml of dichloromethane under cooling in an ice bath, and they were stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, and the product was washed with 0.1 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain the title compound. under cooling in an ice bath the product was washed with 0.1 N hydrochloric acid The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.67 g (40.0 mmol) of EDCl was added to 50 ml of THF solution of 3.50 g (20.0 mmol) of Boc-Gly-OH (manufactured by Tokyo Chemical Industry Co., Ltd), and 1.82 ml (20.0 mmol) of aniline, followed by stirring for 6 hours at room temperature. After a reaction mixture was concentrated under reduced pressure, the concentrate was extracted by adding water and ethyl acetate. After an organic layer was washed with brine (two times for each), and the organic layer was dried over sodium sulfate. After the drying agent was separated by filtration, the filtrate was concentrated under reduced pressure, thereby obtaining crude amide. The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=2/1 to 1/1 (volume ratio)), thereby obtaining 4.85 g of the product with a yield of 96.9%. After a reaction mixture was concentrated under reduced pressure the concentrate was extracted by adding water and ethyl acetate After an organic layer was washed with brine (two times for each), and the organic layer was dried over sodium sulfate After the drying agent was separated by filtration the filtrate was concentrated under reduced pressure obtaining crude amide The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=2/1 to 1/1 (volume ratio))