Trifluoroacetic acid → HCID 90112413, compound

HRID 521715Notes

Reaction equation

HRID 521715 reaction equation
COC1C=CC(C[N:10]2[C:14]3([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH:13]3[CH2:12][O:11]2)=CC=1.FC(F)(F)C(O)=O>ClCCl>[N:28]1[CH:27]=[CH:26][C:25]([C:14]23[CH2:15][NH:16][CH2:17][CH:13]2[CH2:12][O:11][NH:10]3)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90121181HCID 90121181, compound

Product 1

HCID 90112413HCID 90112413, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-[(4-methoxyphenyl)methyl]-6a-(4-pyridyl)-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate (1.3 g, 3.16 mmol) in dichloromethane (30 mL) is added trifluoroacetic acid (7 mL, 94.77 mmol). The resulting solution is stirred at room temperature for 1 hour. The reaction is concentrated and the resulting residue is kept at room temperature overnight. This residue is then loaded onto an ion exchange column and the column is first eluted with methanol followed by 2 M ammonia/methanol solution. The desired basic fraction is collected and concentrated under reduced pressure to give the title compound (592 mg, 98%). ES/MS (m/e): 192 (M+1).

Workup

  1. concentrationThe reaction is concentrated
  2. waitthe resulting residue is kept at room temperature overnight
  3. washthe column is first eluted with methanol
  4. customThe desired basic fraction is collected
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f9dd7d0068843e486d1f0bd37c64cc6
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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