Trifluoroacetic acid → HCID 24830308, compound

HRID 467554Notes

Reaction equation

HRID 467554 reaction equation
C(OC(=O)[NH:7][CH:8]([C:13](=[O:33])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[C:25]([C:27]3[O:28][CH:29]=[CH:30][N:31]=3)[CH:24]=[CH:23][C:22]=2[CH3:32])=[CH:17][CH:16]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl.CO>C(Cl)Cl>[CH3:32][C:22]1[CH:23]=[CH:24][C:25]([C:27]2[O:28][CH:29]=[CH:30][N:31]=2)=[CH:26][C:21]=1[C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:13](=[O:33])[CH:8]([NH2:7])[CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 69287086HCID 69287086, compound

Product 1

HCID 24830308HCID 24830308, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50 ml round bottom flask, was placed [3-Methyl-1-(2′-methyl-5′-oxazol-2-yl-biphenyl-4-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester (370 mg, 0.80 mmol) followed by the slow addition of a solution of 2,2,2-trifluoroacetic acid (3 ml) in DCM (7 ml) with stirring. The resulting solution was allowed to stir at rt for 4 hours. The reaction progress was monitored by TLC (CH2Cl2/MeOH=10:1). The mixture was then concentrated by evaporation under vacuum using a rotary evaporator. Adjustment of the pH to 7-8 was accomplished by the addition of aq NaHCO3 (sat.). The resulting solution was extracted three times with 10 ml of EtOAc and the organic layers combined and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The residue was triturated with 10 ml of n-Hexane to provide 30 mg (21%) of 2-Amino-4-methyl-pentanoic acid (2′-methyl-5′-oxazol-2-yl-biphenyl-4-yl)-amide as a white solid.

Workup

  1. customInto a 50 ml round bottom flask, was placed
  2. stirringto stir at rt for 4 hours
  3. concentrationThe mixture was then concentrated by evaporation under vacuum
  4. customa rotary evaporator
  5. additionAdjustment of the pH to 7-8 was accomplished by the addition of aq NaHCO3 (sat.)
  6. extractionThe resulting solution was extracted three times with 10 ml of EtOAc
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated by evaporation under vacuum
  9. customa rotary evaporator
  10. customThe residue was triturated with 10 ml of n-Hexane

Sources & evidence

ORD record
ord-a9dc46fd2fbc4d34a6621f4ca74a4a1f
Source dataset
uspto-grants-2014_01
Patent number
US08623871B2

Reaction notes

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