Trifluoroacetic acid → HCID 15228076, compound

HRID 1769031Notes

Reaction equation

HRID 1769031 reaction equation
[CH3:1][CH2:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1)=[O:16].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1)=[O:16]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 540144471-[[(2-Ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl)methanone

Product 1

HCID 15228076HCID 15228076, compound

Procedure

Mix 1-[[(2-ethoxy)ethyl]-1H-benzimidazol-2-yl][1-(t-butyloxycarbonyl)-4-piperidinyl]methanone (10.07 g, 26.67 mmol) and trifluoroacetic acid (75 mL). Stir at room temperature until the reaction is complete. Pour onto water and carefully neutralize with solid sodium hydrogen carbonate. Extract into ethyl acetate (2×), wash with brine and dry (MgSO4). Evaporate the solvent in vacuo and purify by chromatography to give the title compound.

Workup

  1. additionPour onto water
  2. extractionExtract into ethyl acetate (2×)
  3. washwash with brine
  4. dry with materialdry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by chromatography

Sources & evidence

ORD record
ord-c2a19692b3094a1c9b0b889db26201ea
Source dataset
uspto-grants-1995_01
Patent number
US05380731

Reaction notes

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