Trifluoroacetic acid → (S)-2-Amino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butan-1-ol

HRID 1455588Notes

Reaction equation

HRID 1455588 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH:11]([OH:28])[C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)=[N:15][N:16]=1)[CH2:9][CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH:8]([CH2:9][CH3:10])[C@@H:11]([C:12]1[O:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]([F:25])([F:27])[F:26])=[CH:21][CH:22]=2)=[N:15][N:16]=1)[OH:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57535328((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 68823850(S)-2-Amino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butan-1-olYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl ester (0.54 mmol, 0.225 g) is dissolved in dichloromethane (9 mL) and treated with trifluoroacetic acid (1 mL). The reaction mixture is stirred for four hours. The solvents are evaporated under reduced pressure. The residue is re-dissolved in dichloromethane (20 mL) and Silicycle Triamine (5.4 mmol, 1.47 g) is added. The reaction mixture is stirred for 60 h (over the weekend). The reaction mixtures are filtered under suction and the solvents evaporated to give (S)-2-Amino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butan-1-ol (0.164 g, 96%). MS: m/z=318 (M+H+)

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. dissolutionThe residue is re-dissolved in dichloromethane (20 mL)
  3. stirringThe reaction mixture is stirred for 60 h (over the weekend)
  4. customThe reaction mixtures
  5. filtrationare filtered under suction
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-9ebffeec6a3544c2b76d1a905ba2af14
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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