Water → HCID 68792808, compound

Participants

Reaction Steps

To a solution of N-({4-[(2R,3R)-3-{[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6,N6-dimethyl-L-lysine (11.0 mg, 0.013 mmol) in MeCN (1 ml) were added scandium tris(trifluoromethanesulfonate) (0.5 mg, 0.00102 mmol) and water (2 μl, 0.131 mmol). The reaction mixture was stirred for 3 hours. Additional Sc(OTf)3 (0.7 mg, 0.00142 mmol) and water (2 μl, 0.131 mmol) were added and the mixture was stirred for 1 hour. Additional Sscandium tris(trifluoromethanesulfonate) (6.0 mg, 0.01219 mmol)) and water (4 μl, 0.262) were added and the reaction mixture was stirred for 1 hour. Ammonium acetate buffer (0.1M, 1 ml) was added. The resulting solution was purified with preparative HPLC on a C8 column, UV 235/285 nm. A gradient from 20 to 43% MeCN was used as eluent. The pure fractions were collected and most of the MeCN was removed under reduced pressure. The residue was lyophilised to give the title compound. H-NMR (500 MHz, DMSO-d6): 1.21-1.31 (m, 2H), 1.33-1.44 (m, 2H), 1.51-1.60 (m, 1H), 1.63-1.71 (m, 1H), 2.16 (s, 6H), 2.25 (bs, 2H), 2.81-2.94 (m, 2H), 3.01-3.15 (m, 2H), 3.78 (d, 2H), 4.07 (bs, 1H), 4.25 (d, 0.5H) 4.26 (d, 0.5H), 4.44-4.50 (m, 2H), 4.52 (s, 2H), 4.59-4.66 (m, 1H), 5.01-5.05 (b, 1H), 6.64 (dd, 1H), 6.97-7.02 (m, 3H), 7.11-7.18 (m, 3H), 7.21-7.26 (m, 2H), 7.37 (d, 2H), 7.98 (bs, 1H), 8.26 (t, 1H). M/z: 721.40 (M−1)

Provenance & Evidence