Trifluoroacetic acid → HCID 178462335, compound

HRID 1424143Notes

Reaction equation

HRID 1424143 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][C:8]2[NH:9][C:10]([C@@H:12]([NH:16]C(=O)OC(C)(C)C)[C@H:13]([OH:15])[CH3:14])=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:16][C@H:12]([C:10]1[NH:9][C:8]2[CH:24]=[CH:25][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][C:7]=2[N:11]=1)[C@H:13]([OH:15])[CH3:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178462344HCID 178462344, compound

Product 1

HCID 178462335HCID 178462335, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl [(1R,2R)-1-(5-tert-butyl-1H-benzimidazol-2-yl)-2-hydroxypropyl]-carbamate (105 mg, 0.302 mmol) was added DCM (5 mL) followed by TFA (700 μL) at 0° C. The reaction was allowed to warm to room temperature for 4 hours before cooling back to 0° C. and quenching with saturated aqueous NaHCO3 solution (20 mL). The mixture was extracted with DCM, the organic layer collected, dried over MgSO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with DCM:MeOH:NH3 (80:20:2) to afford the title compound (21 mg, 28%).

Workup

  1. temperaturebefore cooling back to 0° C.
  2. customquenching with saturated aqueous NaHCO3 solution (20 mL)
  3. extractionThe mixture was extracted with DCM
  4. customthe organic layer collected
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with DCM:MeOH:NH3 (80:20:2)

Sources & evidence

ORD record
ord-2361949c4f0a4de698312022c23e4747
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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