Trifluoroacetic acid → HCID 68157949, compound

HRID 243127Notes

Reaction equation

HRID 243127 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:13]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:26][C:23]1[CH:24]=[CH:25][C:12]2[N:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:13]=2[CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68158115HCID 68158115, compound

Product 1

HCID 68157949HCID 68157949, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

{(S)-1-[6-Fluoro-1-(4-fluorophenyl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester (0.8 g, 2.14 mmol) was dissolved in DCM (10 mL) and TFA (5 mL) added. The reaction mixture was stirred at RT for 1 h. The resultant mixture was concentrated in vacuo to afford a dark green gum. This was dissolved in DCM (40 mL) and stirred vigorously with saturated aqueous NaHCO3 (20 mL) for 10 minutes. The layers were separated and the organic fraction dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 10% MeOH in DCM) to afford the title compound (0.33 g, 57%). LCMS (Method C): RT 1.86 min [M+H]+ 274.2

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. customto afford a dark green gum
  3. customThe layers were separated
  4. dry with materialthe organic fraction dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, 10% MeOH in DCM)

Sources & evidence

ORD record
ord-1805a9b2514a45be9cd73bf98b40869a
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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