Trifluoroacetic acid → HCID 70111126, compound

HRID 1603836Notes

Reaction equation

HRID 1603836 reaction equation
[C:1]([NH:4][CH2:5][CH:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14](C3CCN(C(OC(C)(C)C)=O)CC=3)=[CH:13][CH:12]=2)[CH2:7]1)(=[O:3])[CH3:2].F[C:31](F)(F)[C:32](O)=O>C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>[N:4]1([C:14]2[CH:13]=[CH:12][C:11]([C:8]3[CH2:7][CH:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])[O:10][N:9]=3)=[CH:16][CH:15]=2)[CH2:32][CH:31]=[CH:7][CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11069390HCID 11069390, compound

Product 1

HCID 70111126HCID 70111126, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a flame dried flask containing tert-Butyl 4-[4-[5-[(acetylamino)methyl]-4,5-dihydro-3-isoxazolyl]phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate (270 mg, 0.68 mmol) in methylene chloride (15 mL) at 0° C. is added trifluoroacetic acid (1.04 mL, 13.52 mmol). The reaction is stirred 1 hour at 0° C. and 2 hours at ambient temperature. The reaction is poured over a slurry of ice in saturated potassium carbonate (15 mL). The resulting aqueous phase is extracted with methylene chloride (5×25 mL). The extracts are dried over sodium sulfate concentrated in vacuo to give the title compound, MS (ESI+) for C17H21N3O2 m/z 300.2 (M+H)+.

Workup

  1. customTo a flame dried flask
  2. extractionThe resulting aqueous phase is extracted with methylene chloride (5×25 mL)
  3. dry with materialThe extracts are dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4030f3e251d248d299b6dc13f00e9793
Source dataset
uspto-grants-1999_11
Patent number
US05990136

Reaction notes

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