Reacción #1772040

Ecuación de reacción

methyl 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate

lithium hydroxide monohydrate

sulfuric acid

LiOH

→

lithium 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate

Rendimiento 114.6%

Disolventes

EA

THF

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGto stir overnight at which time TLC
2. 2
   ConcentraciónConcentrated in vacuo

Procedimiento

To methyl 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate (50 mg, 0.246 mmol) in THF (2 mL) and water (0.5 mL) was added lithium hydroxide monohydrate (10.33 mg, 0.246 mmol). The resultant solution was allowed to stir overnite at ambient temperature. TLC (1:1 EA/Hex; Hanessian stain [1 g Ce(NH4)2SO4, 6 g ammonium molybdate, 6 ml sulfuric acid, and 100 ml water]) indicated ˜10% starting material remaining. Added an additional 3 mg LiOH and allowed to stir overnight at which time TLC showed no starting material remaining. Concentrated in vacuo and placed on high vac overnite providing 55 mg lithium 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate as a colorless solid. 1H NMR (500 MHz, MeOD) δ ppm 3.39-3.47 (m, 1H) 3.67 (s, 3H) 4.28 (d, J=7.93 Hz, 1H) 4.64 (t, J=6.26 Hz, 1H) 4.68 (t, J=7.02 Hz, 1H) 4.73 (d, J=7.63 Hz, 2H).

Fuente