Trifluoroacetic acid methylene chloride → HCID 67804264, compound

HRID 2259195Notes

Reaction equation

HRID 2259195 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:32]>>[ClH:32].[N+:21]([C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)([O-:23])=[O:22]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 54214404HCID 54214404, compound

Product 1

HCID 67804264HCID 67804264, compound

Procedure

A 159 mg sample of the BOC-protected intermediate from step 1b above was dissolved in 10 mL of 1:1 TFA/methylene chloride and stirred at room temperature for 16 hr. The solvents were removed by evaporation, and excess 10% aqueous NaHCO3 was added. The solution was extracted 3× with methylene chloride, the extract was dried over MgSO4 and the solvent was removed. The residue was purified by column chromatography on silica gel, eluting with 10:1 chloroform:methanol. The product was dissolved in ether and treated with HCl/ether. The white precipitate was filtered off, washed with ether, and dried under vacuum to afford 71 mg of the title product. MS: 223 (M+H)+, 240 (M+NH4)+. NMR (D2O) δ: 1.91-2.36 (m, 4H), 3.39-3.46 (m, 2H), 4.14 (dq, 1H, J=3.3, 8 Hz), 4.27 (dd, 1H, J=7.7, 10.6 Hz), 4.50 (dd, 1H, J=3.3, 10.6 Hz), 7.42-7.46 (m, 1H), 7.59 (t, 1H, 8 Hz), 7.87 (t, 1H, 2.5), 7.95 (ddd, 1H, J=1, 2, 3.3 Hz). Anal. Calcd for C11H15ClN2O3 : C, 51.07; H, 5.84; N, 10.83; Found: C, 51.01; H, 5.88; N, 10.63.

Workup

  1. customThe solvents were removed by evaporation, and excess 10% aqueous NaHCO3
  2. additionwas added
  3. extractionThe solution was extracted 3× with methylene chloride
  4. dry with materialthe extract was dried over MgSO4
  5. customthe solvent was removed
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with 10:1 chloroform
  8. dissolutionThe product was dissolved in ether
  9. additiontreated with HCl/ether
  10. filtrationThe white precipitate was filtered off
  11. washwashed with ether
  12. customdried under vacuum

Sources & evidence

ORD record
ord-da3decd64f0c40dab9b59567611e873c
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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