Trifluoroacetic acid → HCID 10856182, compound

HRID 469704Notes

Reaction equation

HRID 469704 reaction equation
[CH3:1][O:2][C:3]1([O:19][CH3:20])[C:9]([NH:10]C(=O)OC(C)(C)C)=[CH:8][C:7](=[O:18])[CH:6]2[CH:4]1[O:5]2.FC(F)(F)C(O)=O>ClCCl>[NH2:10][C:9]1[C:3]([O:2][CH3:1])([O:19][CH3:20])[CH:4]2[CH:6]([O:5]2)[C:7](=[O:18])[CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11822201HCID 11822201, compound

Product 1

HCID 10856182HCID 10856182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 4 (300 mg, 1.1 mmol) in anhydrous dichloromethane (6 mL) was stirred in an ice bath under an inert nitrogen atmosphere. To this solution was added trifluoroacetic acid (1.5 mL) drop-wise and the solution was brought to room temperature, stirring 3 hours. After judging complete by thin layer chromatography, the solvents were evaporated and the residue was dissolved in ethyl acetate. Solid sodium bicarbonate (2 g) was carefully added and the solution was stirred 10 minutes. The salt was filtered and rinsed with ethyl acetate before evaporation of the solvent. The crude compound was purified over silica gel using a gradient of ethyl acetate (0 to 100%) in heptane. The product eluted in 100% ethyl acetate giving 178 mg (91%) of compound (5). The 1H NMR of the product was consistent with that reported in the literature (Synthesis 1998, 775).

Workup

  1. customwas brought to room temperature
  2. customthe solvents were evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. additionSolid sodium bicarbonate (2 g) was carefully added
  5. stirringthe solution was stirred 10 minutes
  6. filtrationThe salt was filtered
  7. washrinsed with ethyl acetate before evaporation of the solvent
  8. customThe crude compound was purified over silica gel using a gradient of ethyl acetate (0 to 100%) in heptane
  9. washThe product eluted in 100% ethyl acetate giving 178 mg (91%) of compound (5)
  10. customthat reported in the literature (Synthesis 1998, 775)

Sources & evidence

ORD record
ord-ed3bfe8c8b2f45a9ad90faafceb65e9d
Source dataset
uspto-grants-2014_01
Patent number
US08629164B2

Reaction notes

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