Trifluoroacetic acid → HCID 64128755, compound

HRID 1023429Notes

Reaction equation

HRID 1023429 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][C:15]([OH:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[CH:11]=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[NH2:7][C:8]1[CH:13]=[C:12]([CH2:14][C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([OH:23])[CH3:16])[CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 69083970[4-(2-Hydroxy-2-phenyl-propyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 64128755HCID 64128755, compoundYield 122.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of [4-(2-hydroxy-2-phenyl-propyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (140 mg, 0.43 mmol) in DCM (4 mL) is added trifluoroacetic acid (0.3 mL). The mixture is stirred for 16 hrs at room temperature. Then EtOAc (35 mL) is added followed by the addition of saturated NaHCO3 aquaous solution (15 mL) and water (15 mL). The mixture is stirred for 15 min and the aqueous layer is separated. The aqueous layer is then extracted with EtOAc (2×25 mL). All the organic layers are combined and concentrated to give 120 mg of crude product which is used in the next step without purification.

Workup

  1. stirringThe mixture is stirred for 15 min
  2. customthe aqueous layer is separated
  3. extractionThe aqueous layer is then extracted with EtOAc (2×25 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f578ed60473c44e983c1c754598002a7
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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