Trifluoroacetic acid → HCID 58508568, compound

HRID 454709Notes

Reaction equation

HRID 454709 reaction equation
C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O.C([O:23][C:24]1[CH:50]=[CH:49][C:48]([N:51]2[CH2:56][CH2:55][O:54][CH2:53][CH2:52]2)=[CH:47][C:25]=1[C:26]([NH:28][C:29]1[CH:41]=[C:40]([C:42]2[S:43][CH:44]=[CH:45][CH:46]=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:50]=[CH:49][C:48]([N:51]2[CH2:52][CH2:53][O:54][CH2:55][CH2:56]2)=[CH:47][C:25]=1[C:26]([NH:28][C:29]1[CH:41]=[C:40]([C:42]2[S:43][CH:44]=[CH:45][CH:46]=2)[CH:39]=[CH:38][C:30]=1[C:31]([OH:33])=[O:32])=[O:27]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 66991010HCID 66991010, compound

Product 1

HCID 58508568HCID 58508568, compoundYield 77.8%

Procedure

Thioanisole (2.0 mL) and trifluoroacetic acid (6.8 mL) were added to the obtained tert-butyl 2-(2-(benzyloxy)-5-(morpholin-4-yl)benzamido)-4-(thiophen-2-yl)benzoate (0.19 g), followed by stirring at room temperature for 24 hours. The solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue. The solid substance was collected by filtration, and water and 2-propanol were added to the obtained solid substance. After adjusting the pH to 6.0 with a saturated aqueous solution of sodium bicarbonate, the solid substance was collected by filtration to obtain 0.11 g of 2-(2-hydroxy-5-(morpholin-4-yl)benzamido)-4-(thiophen-2-yl)benzoic acid as a yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. filtrationThe solid substance was collected by filtration, and water and 2-propanol
  4. additionwere added to the obtained solid substance
  5. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-04eb784c68194421818a87ac3513974a
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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