Trifluoroacetic acid → HCID 90111297, compound

HRID 521719Notes

Reaction equation

HRID 521719 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:14]3([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH:13]3[CH2:12][O:11]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][N:10]2[C:14]3([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[CH2:15][NH:16][CH2:17][CH:13]3[CH2:12][O:11]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90121158HCID 90121158, compound

Product 1

HCID 90111297HCID 90111297, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 1-[(4-methoxyphenyl)methyl]-6a-(3-pyridyl)-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate (2.9 g, 7.05 mmol) in dichloromethane (80 mL) is added trifluoroacetic acid (16 mL). The reaction mixture is stirred for 1 hour 30 minutes at room temperature. The solvent is concentrated and the residue is partitioned between saturated aqueous sodium bicarbonate (30 mL) and dichloromethane (100 mL). The resulting solution is stirred for 30 minutes then the phases are separated. The aqueous phase is re-extracted with dichloromethane. The combined dichloromethane extracts are dried over magnesium sulfate, filtered, and concentrated under vacuum to give a residue. The residue is purified by silica gel chromatography using a 0-10% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (1.33 g, 43%). ES/MS (m/e): 312 (M+1).

Workup

  1. concentrationThe solvent is concentrated
  2. customthe residue is partitioned between saturated aqueous sodium bicarbonate (30 mL) and dichloromethane (100 mL)
  3. stirringThe resulting solution is stirred for 30 minutes
  4. customthe phases are separated
  5. extractionThe aqueous phase is re-extracted with dichloromethane
  6. dry with materialThe combined dichloromethane extracts are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give a residue
  10. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-5a509dda760947e9ad1c44578c1201a7
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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