Trifluoroacetic acid → HCID 67529900, compound

HRID 2388235Notes

Reaction equation

HRID 2388235 reaction equation
C1C2C(=CC3C(C=2C[O:16][C:17]2[C:18]4[O:37][N:36]=[C:35]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:19]=4[C:20]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:21][C:22]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24])=CC=CC=3)C=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:28]([C:20]1[C:19]2[C:35]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[N:36][O:37][C:18]=2[C:17]([OH:16])=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86648128HCID 86648128, compound

Product 1

HCID 67529900HCID 67529900, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 7-(anthracen-9-ylmethoxy)-4-benzyl-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (110 mg, 0.23 mmol) was dissolved in 2 mL of CH2Cl2 and cooled in an ice bath. Trifluoroacetic acid (0.18 mL, 2.30 mmol) was added and the mixture was stirred at 0° C. for 20 min. Solvent and excess TFA were evaporated off, and the residue was partitioned between 20 mL of EtOAc and 20 mL of saturated sodium bicarbonate solution. The pH of the mixture was adjusted to 3 by addition of 4M hydrochloric acid. The aqueous layer was extracted with additional EtOAc and the combined organic layer was dried over MgSO4 and concentrated. Purification of the residue by flash chromatography (0-40% EtOAc/hexanes) gave 36 mg of the title compound. MS: (+) m/z 375.37 (M+1).

Workup

  1. temperaturecooled in an ice bath
  2. customSolvent and excess TFA were evaporated off
  3. customthe residue was partitioned between 20 mL of EtOAc and 20 mL of saturated sodium bicarbonate solution
  4. additionThe pH of the mixture was adjusted to 3 by addition of 4M hydrochloric acid
  5. extractionThe aqueous layer was extracted with additional EtOAc
  6. dry with materialthe combined organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customPurification of the residue by flash chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fd922f7097554fba888e4b73f12fd693
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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