Trifluoroacetic acid → HCID 90112018, compound

HRID 521716Notes

Reaction equation

HRID 521716 reaction equation
FC(F)(F)C(O)=O.[N:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[C:14]12[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH:18]1[CH2:17][O:16][NH:15]2>ClCCl>[N:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[C:14]12[CH2:21][NH:20][CH2:19][CH:18]1[CH2:17][O:16][NH:15]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90111971HCID 90111971, compound

Product 1

HCID 90112018HCID 90112018, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (40 mL) is added to a stirred solution of tert-butyl 6a-pyrazin-2-yl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (5.14 g, 17.58 mmol) in dichloromethane (200 mL) at room temperature. The mixture is stirred for 1 hour and the solvents are evaporated under reduced pressure. The resulting residue is dissolved in methanol (100 mL) and loaded onto an ion exchange column (50 g) and the column is first eluted with methanol (110 mL) followed by 7 M ammonia/methanol solution (150 mL). This basic fraction is concentrated under reduced pressure to give a crude product which is further purified by silica gel column chromatography using a 0-10% gradient of 0.14 M ammonia/methanol in dichloromethane to give the title compound (2.4 g, 71%). ES/MS (m/e): 193 (M+1).

Workup

  1. customthe solvents are evaporated under reduced pressure
  2. dissolutionThe resulting residue is dissolved in methanol (100 mL)
  3. washthe column is first eluted with methanol (110 mL)
  4. concentrationThis basic fraction is concentrated under reduced pressure
  5. customto give a crude product which
  6. customis further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1717fd7a41a440d6b7fac69041c5d148
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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