Trifluoroacetic acid → 2-(2-Hydroxy-5-(thiomorpholin-4-yl)benzamido)-4-phenylbenzoic acid

HRID 454601Notes

Reaction equation

HRID 454601 reaction equation
C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O.C([O:23][C:24]1[CH:51]=[CH:50][C:49]([N:52]2[CH2:57][CH2:56][S:55][CH2:54][CH2:53]2)=[CH:48][C:25]=1[C:26]([NH:28][C:29]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:39]=[CH:38][C:30]=1[C:31]([O:33]C(C)(C)C)=[O:32])=[O:27])C1C=CC=CC=1>>[OH:23][C:24]1[CH:51]=[CH:50][C:49]([N:52]2[CH2:53][CH2:54][S:55][CH2:56][CH2:57]2)=[CH:48][C:25]=1[C:26]([NH:28][C:29]1[CH:41]=[C:40]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:39]=[CH:38][C:30]=1[C:31]([OH:33])=[O:32])=[O:27]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 66990549Tert-butyl 2-(2-(benzyloxy)-5-(thiomorpholin-4-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 585087822-(2-Hydroxy-5-(thiomorpholin-4-yl)benzamido)-4-phenylbenzoic acidYield 62.8%

Procedure

Thioanisole (1.0 mL) was added to a trifluoroacetic acid (2.0 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-(thiomorpholin-4-yl)benzamido)-4-phenylbenzoate (0.10 g), followed by stirring at room temperature for 24 hours. The solvent was evaporated under reduced pressure, and a 4 mol/L hydrogen chloride-dioxane solution (0.5 mL) and ethyl acetate (1.0 mL) were added to the residue, followed by stirring at room temperature for 3 hours. The solid substance was collected by filtration, and water and ethyl acetate were added to the obtained solid substance. After adjusting the pH to 6.5 with a saturated aqueous solution of sodium bicarbonate, the organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform] to obtain 0.047 g of 2-(2-hydroxy-5-(thiomorpholin-4-yl)benzamido)-4-phenylbenzoic acid as a yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona 4 mol/L hydrogen chloride-dioxane solution (0.5 mL) and ethyl acetate (1.0 mL) were added to the residue
  3. stirringby stirring at room temperature for 3 hours
  4. filtrationThe solid substance was collected by filtration, and water and ethyl acetate
  5. additionwere added to the obtained solid substance
  6. customthe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform]

Sources & evidence

ORD record
ord-c7b58eeb145a4c6db41bba1f7e02bb91
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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