Sodium Iodide → 3-Butenoicacid,2-[[(1,1-dimethylethoxy)carbonyl]amino]-(9CI)

Participants

Reaction Steps

To a solution of 3 (50 mg, 0.267 mmol) in acetone (5 mL) was added Jones reagent (4 M, 0.2 mL, 0.8 mmol) at 0° C. over 10 min and the reaction mixture was then stirred for 3 h at rt. Excess Jones reagent was quenched by addition of i-PrOH. The acetone and i-PrOH were removed under reduced pressure, and the residue was partitioned between water and ethyl acetate. The organic phase was separated and the product was extracted into saturated aqueous Na2CO3 solution. Acidification of the aqueous phase to pH 4 with acetic acid followed by extraction with ethyl acetate, drying (MgSO4), filtration and evaporation gave Boc-protected vinylglycine (44 mg, 82%): 1H NMR (300 MHz, DMSO-d6) δ1.37 (s, 9H), 4.51 (dd, J=6, 7 Hz, 1H), 5.17 (d, J=10 Hz, 1H), 5.28 (d, J=17 Hz, 1H), 5.87 (ddd, J=6, 10, 17 Hz, 1H), 7.30 (d, J=7 Hz, 1H), 12.65 (br s, 1H); 13C NMR (75 MHZ, CDCl3) δ 28.2, 56.2, 78.2, 117.1, 133.1, 155.2, 172.0; HRMS (FAB, 3-NBA, NaI) calculated for C9H15NO4 Na (M+Na+) 224.0899, observed 224.0893.

Provenance & Evidence