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 2239636Notes

Reaction equation

HRID 2239636 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-e8fe71d1543744ffab28f4a10fac054f
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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