Trifluoroacetic acid → HCID 22709575, compound

HRID 352880Notes

Reaction equation

HRID 352880 reaction equation
C(O[C:6]([CH:8]1[NH:13][CH2:12][C:11]2[O:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[N:16][C:10]=2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:20][O:19][C:17]([C:15]1[O:14][C:11]2[CH2:12][NH:13][CH:8]([CH3:6])[CH2:9][C:10]=2[N:16]=1)=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22709528HCID 22709528, compound

Product 1

HCID 22709575HCID 22709575, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(tert-butoxycarbonyl)-2-methoxycarbonyl-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine (500 mg) in methylene chloride (15 ml) was added trifluoroacetic acid (15 ml) at room temperature, followed by stirring for 10 minutes. The reaction mixture was concentrated under reduced pressure. To the resulting residue were added methylene chloride (20 ml), triethylamine (495 μl), acetic acid (205 μl), formalin (230 μl) and sodium triacetoxyborohydride (570 mg) at room temperature. After stirring for 15 minutes, methylene chloride (20 ml) and a saturated aqueous solution (50 ml) of sodium bicarbonate were added to the reaction mixture to separate it into layers. The water layer was extracted with methylene chloride (3×20 ml). The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (chloroform:methanol=20:1→10:1), whereby the title compound (257 mg) was obtained as a colorless transparent oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the resulting residue were added methylene chloride (20 ml), triethylamine (495 μl), acetic acid (205 μl), formalin (230 μl) and sodium triacetoxyborohydride (570 mg) at room temperature
  3. stirringAfter stirring for 15 minutes
  4. additionmethylene chloride (20 ml) and a saturated aqueous solution (50 ml) of sodium bicarbonate were added to the reaction mixture
  5. customto separate it into layers
  6. extractionThe water layer was extracted with methylene chloride (3×20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by chromatography on a silica gel column (chloroform:methanol=20:1→10:1), whereby the title compound (257 mg)
  11. customwas obtained as a colorless transparent oil

Sources & evidence

ORD record
ord-f3c0219252ce426bb9d5449604c0431b
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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