Trifluoroacetic acid → 3-(2-(2-((Bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoic acid

Participants

Reaction Steps

TFA (6.63 mL, 86 mmol) was added dropwise to a stirred solution of tert-butyl 3-(2-(2-((bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoate (50) (4.5 g, 8.61 mmol) in DCM (43 mL) and the reaction mixture was allowed to stir at RT for 16 h then concentrated in vacuo. The crude product was dissolved in EtOAc (150 mL) and washed with 1M HCl (aq.) (50 mL), water (2×50 mL), and brine (50 mL) the organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford 3-(2-(2-((bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoic acid (51) (3.98 g, 99%) as a colourless oil: m/z 467 (M+H)+ (ES+); 465 (M−H)− (ES−). 1H NMR (400 MHz, CDCl3) δ: 7.36-7.31 (m, 10H), 5.12-5.03 (m, 4H), 4.14-4.09 (m, 2H), 3.69-3.64 (m, 2H), 3.60 (s, 4H), 3.47 (s, 2H), 1.20 (s, 6H).

Provenance & Evidence