Pyridine → (R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonate

HRID 1036446Notes

Reaction equation

HRID 1036446 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([C@:27]1([CH3:33])[CH2:31][O:30][C:29](=[O:32])[NH:28]1)[CH:21]=[CH:20]2.N1C=CC=CC=1.C(Cl)Cl>>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C@:27]3([CH3:33])[CH2:31][O:30][C:29](=[O:32])[NH:28]3)[CH:23]=2)[CH:18]=1)(=[O:5])=[O:4]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 86642894(R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonateYield 88.5%

Procedure

Trifluoromethanesulfonic anhydride (0.144 mL, 0.000859 mol) was slowly added to a solution containing (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (190 mg, 0.00078 mol), pyridine (2 mL, 0.02 mol), and methylene chloride (2 mL, 0.03 mol) at 0° C. After stirring overnight TLC showed complete reaction. After concentration, the crude was purified by chromatography using a 0-100% EtOAc/hexane gradient to give (R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonate as a yellow gel (259 mg, 88%). 1H NMR (400 MHz, CDCl3-d) δ=7.95 (s, 1H), 7.94-7.89 (m, 2H), 7.77 (d, J=1.9 Hz, 1H), 7.59 (dd, J=1.6, 8.6 Hz, 1H), 7.42 (d, J=9.0 Hz, 1H), 4.48 (d, J=8.4 Hz, 1H), 4.43 (d, J=8.4 Hz, 1H), 1.88 (s, 3H).

Workup

  1. customreaction
  2. concentrationAfter concentration
  3. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-b3f48e7a0a2747da8201b25aae680668
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

Loading…