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ChemicalBook CAS DataBase List 3-[(1-ADAMANTYLCARBONYL)AMINO]PROPANOIC ACID
21241-42-9

3-[(1-ADAMANTYLCARBONYL)AMINO]PROPANOIC ACID synthesis

2synthesis methods
-

Yield:-

Reaction Conditions:

with sodium hydrogencarbonate in water;

Steps:

5.A Preparation of O10eq -[N-(1-Adamantanecarbonyl)-β-Alanyl]-Dehydroryanodine (III)

A. N-1-(Adamantanecarbonyl)β-alanine was prepared from 1-adamantanecarbonyl-chloride and β-alanine under modified Schotten-Bauman conditions as follows: A solution 1-adamantanecarbonyl-chloride (10 g., 0.05 mmol) in ether (5 ml.) was added to a vigorously stirred solution of β-alanine sodium salt (6.25 g., 0.055 mmol) and NaHCO3 (5 g., 0.055 mmol) in 10 ml. of water. Stirring was continued for 18 hrs. The solution was acidified with iced concentrated hydrochloric acid, allowed to stand at room temperature for 1 hr. The precipitated solids--a mixture of 1-adamantanecarboxylic acid and the desired 1-adamantanecarbonyl-β-alanine--were filtered, dried in a vacuum desiccator over solid KOH, and then thoroughly digested with ether to remove 1-Adamantanecarboxylic acid. The remaining crystalline material was recrystallized from a chloroform-ether mixture (5:1). to yield 1.2 g. of N-(1-Adamantanecarbonyl)-β-alanine, m.p. 180°-182° C. having the following characteristics:

References:

US5679701,1997,A