Trifluoroacetic acid → HCID 117698115, compound

HRID 1778554Notes

Reaction equation

HRID 1778554 reaction equation
[O:1]=[C:2]1[CH2:7][C:6]2([C:16]([O:18][CH3:19])=[O:17])[N:8]([C:9]([O:11][C:12]([CH3:15])(C)C)=[O:10])[CH:3]1[CH2:4][CH2:5]2.C(O)(C(F)(F)F)=O.C(Cl)(OC[C:31]1[CH:36]=[CH:35]C=[CH:33][CH:32]=1)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][C:6]2([C:16]([O:18][CH3:19])=[O:17])[N:8]([C:9]([O:11][CH2:12][C:15]3[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=3)=[O:10])[CH:3]1[CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10387Benzyl chloroformateHCID 216369877-tert-Butyl 1-methyl 3-oxo-7-azabicyclo[2.2.1]heptane-1,7-dicarboxylate

Product 1

HCID 117698115HCID 117698115, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of O7-tert-butyl O4-methyl 2-oxo-7-azabicyclo[2.2.1]heptane-4,7-dicarboxylate (prepared according to the literature: Org. Lett., Vol. 9, No. 7, 2007 p 1235-p 1238) (0.34 g, 1.27 mmol), TFA (1.5 ml) in DCM was stirred for 2 hours. After removal of solvent and TFA under reduced pressure, the residue was dissolved into DCM (5 mL). To it was added TEA (0.51 g, 5.08 mmol) and CbzCl (0.43 g, 2.54 mmol). After 12 hours, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography to give O7-benzyl O4-methyl 2-oxo-7-azabicyclo[2.2.1]heptane-4,7-dicarboxylate 148b. Yield:30%. MS: calc'd (MH +) 304, measured (MH +) 304.

Workup

  1. customprepared
  2. customAfter removal of solvent and TFA under reduced pressure
  3. dissolutionthe residue was dissolved into DCM (5 mL)
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-741ddb86bf5c4f19b3e7adb640f3f930
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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