Water → N-({4-[(2R,3R)-3-{[(2R)-2-(4-fluorophenyl)-2-hydroxyethyl]thio}-1-(4-{3-[(methylsulfonyl)amino]prop-1-yn-1-yl}phenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-D-lysine

Participants

Reaction Conditions

Reaction Steps

N-({4-[(2R,3R)-3-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-fluorophenyl)ethyl]thio}-1-(4-{3-[(methylsulfonyl)amino]prop-1-yn-1-yl}phenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysine (Method 2) (21.9, 0.022 mmol) was dissolved in MeCN (1.5 ml). Cerium(4+) tetranitrate-nitric acid (1:2) diammoniate (25.1 mg, 0.046 mmol) and water (50 μl) were added. The reaction mixture was heated at 45° C. for 6 h and 30 minutes and it was allowed to stand at room temperature over the weekend. The solution was purified with preparative HPLC on a C8 column, UV 235/285 nm. A gradient from 10 to 90% MeCN in 0.1M NH4OAc buffer was used as eluent. Most of the MeCN was removed under reduced pressure and the residue was lyophilised to give the title compound as a yellow solid. H-NMR (500 MHz, DMSO-d6): 1.13-1.66 (m, 6H), 2.64-2.71 (m, 2H), 2.90-2.96 (m, 2H), 2.97 (s, 3H), 3.62-3.80 (m, 3H), 4.00 (s, 2H), 4.34 (d, 1H), 4.53 (s, 2H), 4.72 (t, 1H), 5.09 (d, 1H), 6.99 (d, 2H), 7.07-7.13 (m, 2H), 7.20 (d, 2H), 7.32-7.40 (m, 6H), 7.46 (b, 1H), 8.42 (t, 1H). M/z: 782.58 (M−1) and 784.42 (M+1).

Provenance & Evidence