Trifluoroacetic acid → HCID 58016825, compound

HRID 1926881Notes

Reaction equation

HRID 1926881 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:15]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[C:21]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:20][C:16]=2[N:17]=[CH:18][N:19]=1)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]2[C:15]3[C:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][NH2:7])=[N:19][CH:18]=[N:17][C:16]=3[O:20][C:21]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 58016917HCID 58016917, compound

Product 1

HCID 58016825HCID 58016825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 380 mg (0.76 mmol) of the compound from Stage 1 in 5 ml methylene chloride and add 0.4 ml anisole and then 5.5 ml trifluoroacetic acid. Stir for 2 h at room temperature. Dilute the mixture with dichloromethane and wash with sodium hydrogencarbonate solution until reaction is neutral. After washing the organic phase with saturated sodium chloride solution, dry over magnesium sulphate. The residue left after concentration by evaporation is dissolved in ethanol and concentrated by evaporation; this operation is repeated three times. 349 mg (82% of theor.) of the title compound is obtained as a yellowish foam.

Workup

  1. washwash with sodium hydrogencarbonate solution until reaction
  2. washAfter washing the organic phase with saturated sodium chloride solution
  3. dry with materialdry over magnesium sulphate
  4. waitThe residue left
  5. concentrationafter concentration
  6. customby evaporation
  7. dissolutionis dissolved in ethanol
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-15a511b26ad842ccaa72de8bc4567618
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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