Methyl 3-Hydroxybenzoate → Methyl 3-{3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propoxy}benzoate

HRID 2422037Notes

Reaction equation

HRID 2422037 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CC1C=CC(S(O[CH2:23][CH2:24][CH2:25][NH:26][C:27]2[C:28](=[O:44])[N:29]([C:40]([CH3:43])([CH3:42])[CH3:41])[S:30](=[O:39])(=[O:38])[C:31]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=O)=O)=CC=1>>[C:40]([N:29]1[C:28](=[O:44])[C:27]([NH:26][CH2:25][CH2:24][CH2:23][O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[C:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[S:30]1(=[O:38])=[O:39])([CH3:41])([CH3:42])[CH3:43]

Participants

3

Reactant 2

HCID 88068Methyl 3-HydroxybenzoateHCID 866258673-[(2-Tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate

Product 1

HCID 11590958Methyl 3-{3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propoxy}benzoateYield 54%

Procedure

The title compound was prepared as described for Example 12 from methyl 3-hydroxybenzoate and 3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate with a reaction time of 15 mins. The reaction mixture was evaporated and the residue purified by silica gel column chromatography (Horizons Biotage) using DCM as eluent to give the title compound (0.077 g, 54%). 1H NMR (500 MHz CDCl3): δ 7.66 (d, 1H), 7.54-7.48 (m, 3H), 4.47-7.42 (m, 3H), 7.36 (t, 1H), 7.07 (dd, 1H), 5.70 (t, 1H), 3.94-3.90 (m, 5H), 3.13-3.08 (m, 2H), 1.90-1.84 (m, 2H), 1.75 (s, 9H); 13C NMR (125 MHz CDCl3): δ 167.1, 159.8, 158.5, 135.3, 131.8, 131.7, 129.8, 129.7, 128.8, 125.3, 122.6, 120.2, 114.6, 107.3, 66.2, 61.7, 52.4, 42.3, 28.9, 27.8; Mass Spectrum M+H+ 473.

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was evaporated
  3. customthe residue purified by silica gel column chromatography (Horizons Biotage)

Sources & evidence

ORD record
ord-558eaa6361064e38914d0215b760287a
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

Loading…