Trifluoroacetic acid → HCID 44434940, compound

HRID 131019Notes

Reaction equation

HRID 131019 reaction equation
C(OC(=O)[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30](=[O:34])[NH:31][CH2:32]C)=[CH:26][N:25]=2)=[CH:19][CH:18]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:32][NH:31][C:30](=[O:34])[C:27]1[CH:28]=[CH:29][C:24]([O:23][C:20]2[CH:21]=[CH:22][C:17]([CH2:16][NH:7][CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:18][CH:19]=2)=[N:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59730317HCID 59730317, compound

Product 1

HCID 44434940HCID 44434940, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine [4-(5-Ethylcarbamoyl-pyridin-2-yloxy)-benzyl]-phenethyl-carbamic acid tert-butyl ester (55.4 mg, 0.12 mmol), CH2Cl2 (4 mL), and TFA 99% (0.8 mL) in a 7 mL reaction vial. After reaction shakes on shaker at room temperature for 24 hours, concentrate under reduced pressure. Add the reaction mixture to a 2 g SCX column, wash with MeOH, and elute with 1N NH3 MeOH. Concentrate sample to afford 41.2 mg (95% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 1.5 (1H, br m), 2.7-3.0 (7H, m), 3.7 (2H, s), 6.2 (1H, br s), 6.9 (1H, d), 7.0-7.4 (9H, m), 8.0 (1H, d), 8.4 (1H, s); MS m/z 363 (M+1).

Workup

  1. customAfter reaction
  2. concentrationconcentrate under reduced pressure
  3. additionAdd the reaction mixture to a 2 g SCX column
  4. washwash with MeOH
  5. washelute with 1N NH3 MeOH
  6. concentrationConcentrate sample

Sources & evidence

ORD record
ord-23c8080ab0584c37b7e1a3f0389c5038
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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