Reaction #985279

Reaction equation

p-Nitro-β-phenylalanine

sodium hydroxide

acetic anhydride

sodium hydroxide

HCl

→

acetyl-p-nitro-β-phenylalanine

Yield 96.9%

Solvents

water

Conditions

Workup

1. 1
   workup.STIRRINGstirred for one hour
2. 2
   Otherthe resulting precipitated crystal
3. 3
   Filtrationwas filtered
4. 4
   Otherdried under reduced pressure

Procedure

p-Nitro-β-phenylalanine (10.0 g, 48 mmol) was mixed with 40 ml of water and adjusted to pH 14 with 25% sodium hydroxide aqueous solution. After being cooled to 5° C., 10.7 ml of acetic anhydride (105 mmol) and 25% sodium hydroxide aqueous solution were simultaneously dropped into the mixture to keep it at a pH range of 11.5˜12 and the resulting mixture was stirred for 1.5 hours at a room temperature. After the mixture was adjusted to pH 2 with conc. HCl and stirred for one hour, the resulting precipitated crystal was filtered and dried under reduced pressure to give 11.6 g of acetyl-p-nitro-β-phenylalanine at a yield of 96.9%.

Source