Trifluoroacetic acid → HCID 19605558, compound

HRID 1603435Notes

Reaction equation

HRID 1603435 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[C:10]([NH:15][C:16](OC(C)(C)C)=[O:17])([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:14][CH:13]2[C:10]([NH:15][CH:16]=[O:17])([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19605556HCID 19605556, compound

Product 1

HCID 19605558HCID 19605558, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.8 g of 3-benzyl-1-(t-butoxycarbonylamino)-3-azabicyclo[3.2.0]heptane was dissolved in 20 ml of methylene chloride, and 50 ml of trifluoroacetic acid was added thereto, followed by stirring for 3 hours. The reaction mixture was concentrated, mixed with an aqueous solution of sodium hydroxide under cooling with ice, and extracted with chloroform. After the extract was dried over anhydrous magnesium sulfate, the chloroform was distilled off. The resulting crude product was dissolved in 47 ml of formic acid, and 17 g of acetic anhydride was added dropwise thereto, under cooling with ice, over a period of 90 minutes. After the addition of ice water, the resulting mixture was neutralized by the addition of an aqueous solution of sodium hydroxide under cooling with ice, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (using a 30:1 mixture of chloroform and methanol as the eluent) to obtain 3.1 g of 3-benzyl-1-formylamino-3-azabicyclo[3.2.0]heptane.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionmixed with an aqueous solution of sodium hydroxide
  3. temperatureunder cooling with ice
  4. extractionextracted with chloroform
  5. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  6. distillationthe chloroform was distilled off
  7. dissolutionThe resulting crude product was dissolved in 47 ml of formic acid
  8. addition17 g of acetic anhydride was added dropwise
  9. temperatureunder cooling with ice, over a period of 90 minutes
  10. additionAfter the addition of ice water
  11. additionthe resulting mixture was neutralized by the addition of an aqueous solution of sodium hydroxide
  12. temperatureunder cooling with ice
  13. extractionextracted with ethyl acetate
  14. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe resulting residue was purified by silica gel column chromatography (
  17. additiona 30:1 mixture of chloroform and methanol as the eluent)

Sources & evidence

ORD record
ord-3263be3e079c4ed8806edfab4fe94b83
Source dataset
uspto-grants-1999_11
Patent number
US05990106

Reaction notes

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