Trifluoroacetic acid → HCID 178436665, compound

HRID 333797Notes

Reaction equation

HRID 333797 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:50])([CH:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][C:25]3[N:29](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:28]=[N:27][N:26]=3)=[CH:17][C:16]=2[Cl:49])[CH3:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:50])([CH:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][C:25]3[NH:29][N:28]=[N:27][N:26]=3)=[CH:17][C:16]=2[Cl:49])[CH3:14])[C:9]([F:11])([F:10])[F:12])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574499702-(2-Chloro-pyridin-4-yl)-3-{2-chloro-4-[3-(1-trityl-(1H)-tetrazol-5-yl)-propoxy]-phenyl}-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 178436665HCID 178436665, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Chloro-pyridin-4-yl)-3-{2-chloro-4-[3-(1-trityl-(1H)-tetrazol-5-yl)-propoxy]-phenyl}-1,1,1-trifluoro-butan-2-ol (80 mg, from previous step) was dissolved in CH2Cl2 (2.5 mL). To the solution was added trifluoroacetic acid (1.25 mL) at RT and the mixture was allowed to stir for 48 hours; almost complete conversion was observed. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate and water. The layers were separated and the organic extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane) to give the desired compounds as a white solid (46 mg). MS (m/e)=476.1 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane)

Sources & evidence

ORD record
ord-d15b046494f04cec8451885595ed9556
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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