2-ethoxy-2-methylpropanamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A −78° C. solution of 2-ethoxy-2-methylpropanamide (1.1 g, 8.39 mmol) in THF (37 mL), under Ar, was treated with LiHMDS (1 M in THF, 11 mL, 11 mmol) stirred for 0.5 h, treated with a solution of isopropenyl chloroformate (1.46 g, 12.10 mmol) in THF (2 mL), stirred for 15 minutes at −78° C. then slowly warmed to RT as the cooling bath expired. The mixture was treated with satd. NH4Cl, extracted with DCM (4×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford prop-1-en-2-yl (2-ethoxy-2-methylpropanoyl)carbamate (2.0 g, 84%) as an orange oil. stirred for 15 minutes at −78° C. The mixture was treated with satd NH4Cl, extracted with DCM (4×) the combined organics were dried over MgSO4 concentrated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-ethoxy-2-methylpropanoic acid (1.1 g, 8.32 mmol) in MeCN (15 mL) was treated with EDC (1.596 g, 8.32 mmol) and HOBT (1.275 g, 8.32 mmol), stirred at RT for 2 h, treated with NH4OH (˜15M, 1.7 mL, ˜25.5 mmol) and stirred at RT overnight. The mixture was treated with satd. NaHCO3 and water, extracted with EtOAc (5×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford 2-ethoxy-2-methylpropanamide (1.1 g, 101%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.03 (s, 2H), 3.31 (q, J=7.0 Hz, 2H), 1.21 (s, 6H), 1.10 (t, J=7.0 Hz, 3H). stirred at RT overnight The mixture was treated with satd NaHCO3 and water, extracted with EtOAc (5×) the combined organics were dried over MgSO4 concentrated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-ethoxy-2-methylpropanoic acid (1.1 g, 8.32 mmol) in MeCN (15 mL) was treated with EDC (1.596 g, 8.32 mmol) and HOBT (1.275 g, 8.32 mmol), stirred at RT for 2 h, treated with NH4OH (˜15M, 1.7 mL, ˜25.5 mmol) and stirred at RT overnight. The mixture was treated with satd. NaHCO3 and water, extracted with EtOAc (5×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford 2-ethoxy-2-methylpropanamide (1.1 g, 101%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.03 (s, 2H), 3.31 (q, J=7.0 Hz, 2H), 1.21 (s, 6H), 1.10 (t, J=7.0 Hz, 3H). stirred at RT overnight The mixture was treated with satd NaHCO3 and water, extracted with EtOAc (5×) the combined organics were dried over MgSO4 concentrated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A −78° C. solution of 2-ethoxy-2-methylpropanamide (1.1 g, 8.39 mmol) in THF (37 mL), under Ar, was treated with LiHMDS (1 M in THF, 11 mL, 11 mmol) stirred for 0.5 h, treated with a solution of isopropenyl chloroformate (1.46 g, 12.10 mmol) in THF (2 mL), stirred for 15 minutes at −78° C. then slowly warmed to RT as the cooling bath expired. The mixture was treated with satd. NH4Cl, extracted with DCM (4×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford prop-1-en-2-yl (2-ethoxy-2-methylpropanoyl)carbamate (2.0 g, 84%) as an orange oil. stirred for 15 minutes at −78° C. The mixture was treated with satd NH4Cl, extracted with DCM (4×) the combined organics were dried over MgSO4 concentrated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-ethoxy-2-methylpropanoic acid (1.1 g, 8.32 mmol) in MeCN (15 mL) was treated with EDC (1.596 g, 8.32 mmol) and HOBT (1.275 g, 8.32 mmol), stirred at RT for 2 h, treated with NH4OH (˜15M, 1.7 mL, ˜25.5 mmol) and stirred at RT overnight. The mixture was treated with satd. NaHCO3 and water, extracted with EtOAc (5×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford 2-ethoxy-2-methylpropanamide (1.1 g, 101%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.03 (s, 2H), 3.31 (q, J=7.0 Hz, 2H), 1.21 (s, 6H), 1.10 (t, J=7.0 Hz, 3H). stirred at RT overnight The mixture was treated with satd NaHCO3 and water, extracted with EtOAc (5×) the combined organics were dried over MgSO4 concentrated to dryness