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ChemicalBook CAS DataBase List CHLOROAC-ASP-OH
67036-33-3

CHLOROAC-ASP-OH synthesis

1synthesis methods
-

Yield:67036-33-3 62%

Reaction Conditions:

with sodium hydroxide;sodium chloride in water;ethyl acetate;

Steps:

1 EXAMPLE 1

EXAMPLE 1 After 24 g (0.18 mol) of L-aspartic acid was suspended in 100 ml of water, 25 ml of 27% sodium hydroxide was added to the suspension to dissolve the acid. While stirring, 25 g (0.22 mol) of chloroacetyl chloride and 27% sodium hydroxide were added dropwise to the solution below 10°C in order to keep the pH in the range of 11.0 to 12.0. The amount of 27% sodium hydroxide required for completion of the dropwise addition was 77 ml. After completion of the addition of NaOH, the mixture was stirred for a further 30 minutes at 15°C. The pH was adjusted to 1.5 with 35% hydrochloric acid. In the reaction mixture was dissolved 20 g of sodium chloride, followed by extraction of the reaction mixture 3 times with 250 ml of ethyl acetate. The ethyl acetate extracts were combined, dried over anhydrous sodium sulfate and then concentrated to give 25 g of crude N-chloroacetyl-L-aspartic acid as an oil. HPLC analysis reveals that the purity was 94% (yield, 62%). The product was used for the next step of amination, as it was. 1H NMR (D2O) δ 3.00 (m, 2H), δ 4.08 (s, 2H), δ 4.84 (m, 1H)

References:

EP493812,1992,A1

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