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LCMS identification of Impurities in 3-amino-2,2-dimethylpropanamide

IP.com Disclosure Number: IPCOM000204400D
Publication Date: 2011-Feb-23
Document File: 1 page(s) / 64K

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LCMS identification of Impurities in 3-amino-2,2-dimethylpropanamide

O

Cl +

O

DCM

O

O

H2N

NH2

Et3N

N

H

NH2

I, C12H16N2O2

N

H

O

N

H

O O

NH2

(tentative structure)

II, C17H25N3O3

O

N

H

O O

N

H

O

NH2

N

H

(tentative structure)

III, C22H34N4O4

I

Benzoyl chloride (4.4 g, 0.031 mol) was added to a solution of 3-amino-2,2- dimethylpropanamide (3.0 g, 0.026 mol) and triethylamine (3.9 g, 0.04 mol) in dichloromethane (50 mL). The mixture was stirred at 20 °C overnight, quenched with 10% sol. of citric acid, the organic layer was separated and washed with brine.

The organic layer was evaporated and analyzed by LCMS/ESI to give: [M+H]+ = 221, [M+Na]+ = 243, [M+K]+ = 259 (I, C12H16N2O2, MW 220) [M+H]+ = 320, [M+Na]+ = 342, [M+K]+=358 (II, C17H25N3O3, MW 319) [M+H]+ = 419, [M+Na]+ = 441, [M+K]+= 457 (III, C22H34N4O4, MW 418)