Aminoisobutyric acid → Alanine, 2-methyl-N-(3-sulfopropyl)-

To a cold (5° C.) mixture of 2-aminoisobutyric acid (2.0 g, 19.4 mmol), NaOH (776 mg, 19.4 mmol) in 1,4-dioxane (10 mL) and water (4 mL) was added via syringe pump (over a 4-hour period), a solution 1,3-propane sultone (2.02 g, 16.2 mmol) in 1,4-dioxane (total: 4 mL). The solution was stirred at room temperature for 2 hours before it was allowed to warm up to room temperature. The reaction mixture was stirred under these conditions overnight. The solvent was evaporated under reduced pressure. The resultant solid material was recrystallized from 5% water/EtOH. The resulting solid was dissolved in water; and the aqueous solution was passed through an ion exchange column (Dowex 50WX 8, 100 g, solvent: water). The solvent was evaporated under reduced pressure. The product was lyophilized to afford Compound DI (880 mg, 28%). 1H NMR (D2O, 500 MHz) 8 ppm 3.00 (t, 2H, J=7.6 Hz), 2.91 (t, 2H, J=7.3 Hz), 2.01 (m, 2H), 1.34 (s, 6H). 13C NMR (D2O, 125 MHz) 8 ppm 176.93, 63.89, 48.13, 42.04, 22.15, 21.86. ES-MS 224 (M−1).

1. temperatureto warm up to room temperature
2. stirringThe reaction mixture was stirred under these conditions overnight
3. customThe solvent was evaporated under reduced pressure
4. customThe resultant solid material was recrystallized from 5% water/EtOH
5. dissolutionThe resulting solid was dissolved in water
6. customThe solvent was evaporated under reduced pressure
7. customto afford Compound DI (880 mg, 28%)

ORD record

ord-6169b3c80b8e429c9c8a888cf7005a0b

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642801B2