Trifluoroacetic acid → HCID 18974090, compound

HRID 2395058Notes

Reaction equation

HRID 2395058 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH2:17][C:18]2[CH:30]=[CH:29][C:21]([C:22]([O:24]C(C)(C)C)=[O:23])=[CH:20][CH:19]=2)=[CH:13][N:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:29][CH:30]=2)=[CH:13][N:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18974130HCID 18974130, compound

Product 1

HCID 18974090HCID 18974090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[3-(4-(benzyloxy)pyrimid-5-yl)propyl]benzoate (0.36 g, 0.92 mmol) was dissolved in dichloromethane (0.7 ml) and treated with trifluoro-acetic acid (1.05 g, 9.2 mmol). The reaction was stirred at amibent temperature for 2 hours. The mixture was partitioned between EtOAc/water and the aqueous layer extracted with EtOAc. The organic layers were combined, dried (MgSO4) and evaporated and the solid was triturated with hexane and recrystallised from isopropanol/water. The cream coloured solid was taken up in THF, filtered through Celite and evaporated to give the title product.

Workup

  1. customThe mixture was partitioned between EtOAc/water
  2. extractionthe aqueous layer extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe solid was triturated with hexane
  6. customrecrystallised from isopropanol/water
  7. filtrationfiltered through Celite
  8. customevaporated

Sources & evidence

ORD record
ord-e10b1ea091dc4fd9b1792446c5b2f8ee
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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