Thioglycolic Acid → HCID 86666542, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-aminopropylcarbamate (85b, 2 g, 11.48 mmoles) in toluene (8 mL), in a pressure tube, was added 900 μL of thioglycolic acid (12.95 mmoles). Argon was bubbled through the solution for 15 min, and the mixture was capped and heated to 115° C. (bath temperature) for 24 h. The solution was then concentrated to dryness in vacuo and the residue was subjected to SiO2 chromatography on a Biotage™ flash chromatography system using 25-0% hexanes in EtOAc as the eluent to furnish 91 (1.19 g, 4.77 mmoles, 42% yield) as a colourless oil. 1H NMR (400 MHz, CDCl3) δ 1.65 (quintet, J=6.3 Hz, 2H), 1.94 (t, J=9.0 Hz, 1H), 3.17 (t, J=6.2, 2H), 3.24 (d, J=8.9 Hz, 2H), 3.33 (q, J=6.3 Hz, 2H), 4.11 (q, J=7.1 Hz, 1H), 4.87 (broad s, 1H), 7.12 (broad s, 1H).

Provenance & Evidence