反应详情

温度

10 °C

200 mL of water and 91 mL of acetone were mixed and 72.4 g (344 mmol) of 4-nitro-L-phenylalanine was added thereto and cooled down to 10° C. or lower. 68 mL of 6M sodium hydroxide aqueous solution was added dropwise to the solution so that the temperature thereof did not exceed 15° C. Keeping around pH 14, 73.58 g (344 mmol) of 2,6-dichlorobenzoyl chloride was slowly added dropwise thereto. In order to keep around pH 14, if needed, a sodium hydroxide aqueous solution was added dropwise. 2 hours later of completion of drop, 86 mL of 6M hydrochloric acid was added with keeping the temperature of the reaction solution at 15° C. or lower to precipitate white crystals. After maturing at 10° C. or lower, the crystals were separated, dried under reduced pressure at 60° C. to obtain 128.5 g of Nα-(2,6-dichlorobenzoyl)-4-nitro-L-phenylalanine. (Yield: 97%) 1H NMR (400 MHz, DMSO-d6): 9.12 (d, 1H, J=8.42 Hz), 8.16 (d, 2H, J=8.78 Hz), 7.59 (d, J=8.77Hz), 7.42 (m, 3H), 3.29 (m), 3.07 (dd, 1H, J=3.64 and 10.42 Hz). 13C NMR (100 MHz, DMSO-d6): 172.25, 163.74, 146.68, 146.18, 131.51, 131.37, 131.05, 128.37, 123.55, 53.17, 36.74.

1. customthereof did not exceed 15° C
2. additionwas slowly added dropwise
3. customat 15° C.
4. customlower to precipitate white crystals
5. customAfter maturing at 10° C.
6. customlower, the crystals were separated
7. customdried under reduced pressure at 60° C.