ChemicalBook CAS DataBase List AZIDOACETIC ACID

AZIDOACETIC ACID synthesis

13synthesis methods

Product Name:AZIDOACETIC ACID
CAS Number:18523-48-3
Molecular formula:C2H3N3O2
Molecular Weight:101.06

56-40-6 Synthesis

56-40-6
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$5.00/25g

18523-48-3
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$54.00/1g

Yield:18523-48-3 90%

Reaction Conditions:

with triflic azide;potassium carbonate;copper(II) sulfate in methanol;dichloromethane;water at 20;

Steps:

3.2 3.2 Gly-azide NI1594 [N₃-Gly-OH]
A solution of NaN₃ (455 mg, 7 mmol) in 1 .2 ml water was added in ice bath and treated with 2 ml of CH₂CI_2. The resulting biphasic mixture was stirred vigorously and treated with Tf₂0 (192 μΙ, 1 .4 mmol) over period of 5 min. The reaction mixture was stirred in a ice bath for 2h, then the organic phase was separated and the aqueous phase was extracted with CH₂CI₂ (2 x 2 ml). The combined organic phase were washed with saturated NaHC0₃ (3 ml) and use immediately without further purification. Commercial compound Glycine, ( 54 mg, 0.7 mmol) was dissolved in 2.5 ml of water and treated with potassium carbonate (K₂C0₃, 145 mg, 1 .01 mmol) and CuS0₄ hydrate (1.7 mg 7 μηηοΙ in 0.4 ml water) were added to the flask consecutively. Freshly prepared dichloromethane solution of TfN₃ was then added, and the solution was brought to homogeneity by adding MeOH (ca.1.3 ml). The resulting solution was stirred at room temperature overnight. The only organic phase (MeOH/ CH₂CI₂) was evaporated under vacuum and the remaining aqueous solution was poured into 6 ml of water and the pH value was adjusted to 6 with 0.1 N HCI solution and added to 8 ml of phosphate buffer (0.02M pH=6.2). The acid aqueous phase was washed with AcOEt (4 x 5 ml) and then concentrated to 1/2 of initial volume, acidified around pH =2 with 0.1 N HCI solution and then extracted with AcOEt (5 x 10 ml). The combined organic phase were washed with brine (20 ml), dried over anhydrous Na₂S0₄, filtered and concentrated to give white liquid (64 mg, yield 90 %). The final product was used without further purification and it structure confirmed by ¹H-NMR analysis (300 MHz): δ (ppm, CDCI₃), 3.97( 2H, s, -CH₂-) and Mass spectroscopy ESI-Tof (m/z) [M+H⁺]= 102.12

References:

LEADIANT BIOSCIENCES SA IN LIQUIDAZIONE;GIANNINI, Giuseppe;NAGGI, Annamaria;ESPOSITO, Emiliano WO2018/188990, 2018, A1 Location in patent:Page/Page column 41

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