Trifluoroacetic acid → HCID 117697925, compound

HRID 1778542Notes

Reaction equation

HRID 1778542 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:13][CH:12]2[N:14]([C:15]([O:17][C:18]([CH3:21])(C)C)=[O:16])[CH:8]([CH2:9][O:10][CH2:11]2)[C:7]1=[O:22])[CH3:2].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+].C(N(CC)C(C)C)(C)C.ClC(OC[C:51]1[CH:56]=[CH:55]C=[CH:53][CH:52]=1)=O>CN(C)C=O.ClCCl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:13][CH:12]2[N:14]([C:15]([O:17][CH2:18][C:21]3[CH:55]=[CH:56][CH:51]=[CH:52][CH:53]=3)=[O:16])[CH:8]([CH2:9][O:10][CH2:11]2)[C:7]1=[O:22])[CH3:2]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 117698042HCID 117698042, compound

Product 1

HCID 117697925HCID 117697925, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Step II and III: a mixture of tert-butyl 7-(2-ethoxy-2-oxo-ethyl)-6-oxo-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate 125b (654 mg, 2.0 mmol), trifluoroacetic acid (1.0 mL) and dichloromethane (2.0 mL) was stirred at room temperature for one hour. The reaction mixture was concentrated. The residue was dissolved in dimethylformamide (5.0 mL), followed by adding potassium carbonate (700 mg, 5.0 mmol) and N,N-diisopropylethylamine (0.3 mL). The result mixture was warmed to 40° C., then added dropwise benzyl chloroformate (311 μL, 2.2 mmol) in dimethylformamide (1.0 mL). The resulting mixture was stirred for another two hours. The reaction was quenched by adding ice-water, extracted with PE: EA=5:1 (30 mL) three times. The combined organic phases were dried over Na2SO4, and concentrated. The residue was purified by silica gel column to give benzyl 7-(2-ethoxy-2-oxo-ethyl)-6-oxo-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate 125d (650 mg, yield: 90%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in dimethylformamide (5.0 mL)
  3. temperatureThe result mixture was warmed to 40° C.
  4. stirringThe resulting mixture was stirred for another two hours
  5. customThe reaction was quenched
  6. additionby adding ice-water
  7. extractionextracted with PE
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-c2b1ada20f8546ae868b44fb327960af
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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