4-Hydroxybenzoic Acid → 3-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-hydroxybenzoate

HRID 2239642Notes

Reaction equation

HRID 2239642 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][CH2:13][CH2:14]Br)=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:6]1(=[O:23])=[O:22])([CH3:4])([CH3:3])[CH3:2].[OH:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1.Cl>>[OH:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([O:31][CH2:14][CH2:13][CH2:12][NH:11][C:8]2[C:9](=[O:10])[N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6](=[O:23])(=[O:22])[C:7]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:30])=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 67242780HCID 67242780, compound

Product 1

HCID 116911023-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-hydroxybenzoateYield 21%

Procedure

The title compound was prepared as described for Example 5 from 2-tert-butyl-4-[(3-bromopropyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxide and 4-hydroxybenzoic acid with a reaction time of 1.5 h. The reaction mixture was acidified with HCl (1N) and extracted with EtOAc. The organic layers were combined and evaporated to dryness. The residue was triturated in MeOH, the solvent was decanted and the residue was purified by silica gel column chromatography (Horizons Biotage) using 50% EtOAc in petroleum ether 40-60° C. as eluent to give the title compound (0.028 g, 21%). 1H NMR (500 MHz CD3CN): δ 7.80 (d, 2H), δ 7.62 (bs, 1H), 7.56-7.48 (m, 2H), 7.56-7.42 (m, 3H), 5.93 (t, 1H), 4.09 (t, 2H), 3.08-3.03 (m, 2H), 1.76-1.68 (m, 1H); 13C NMR (125 MHz CD3CN): δ 166.5, 160.6, 159.8, 135.2, 132.2, 131.8, 129.9, 128.9, 125.0, 122.2, 115.5, 107.4, 62.2, 61.1, 41.1, 28.4, 27.1; Mass Spectrum: M+H+ 459.

Workup

  1. customThe title compound was prepared
  2. extractionextracted with EtOAc
  3. customevaporated to dryness
  4. customThe residue was triturated in MeOH
  5. customthe solvent was decanted
  6. customthe residue was purified by silica gel column chromatography (Horizons Biotage)
  7. custom50% EtOAc in petroleum ether 40-60° C.

Sources & evidence

ORD record
ord-2b418450318b496e9197438973227f79
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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