Hydrochloric Acid → Glycine, N-[(1,1-dimethylethoxy)carbonyl]glycyl-N-methyl-

Participants

Reaction Steps

Lithium hydroxide monohydrate (598 mg, 14.3 mmol) was added to a solution of 200 (1.22 g, 4.7 mmol) in 20 mL of THF—CH3OH—H2O (3:1:1) at 25° C. and the resulting reaction mixture was stirred for 3 h. The reaction mixture was poured onto 3M aqueous HCl (10 mL) and extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo to give 300 (1.16 g, 1.16 g theoretical, 100%) as a colorless oil. This acid was identical to authentic material14 and was used directly in the next step without further purification: 1H NMR (CDCl3, 400 MHz)14 5.76 and 5.66 (two br s, 1H), 4.11, 4.00, and 3.91 (three s, 4H), 2.99 and 2.95 (two s, 3H), 1.38 (s, 9H); IR (neat)max 3348, 2979, 2937, 1717, 1654, 1691, 1409, 1368, 1287, 1252, 1167, 1053, 1030, 954, 866, 782, 736 cm−1.

Provenance & Evidence