Trifluoroacetic acid → HCID 23598686, compound

HRID 891188Notes

Reaction equation

HRID 891188 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]1[CH2:11][CH:10]=[CH:9][CH2:8][CH:7]([NH:12]C(OC(C)(C)C)=O)[C:6]1=[O:20].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][N:5]1[CH2:11][CH:10]=[CH:9][CH2:8][CH:7]([NH2:12])[C:6]1=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15235395Methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,3,4,7-tetrahydro-2-oxo-1H-azepine-1-acetate

Product 1

HCID 23598686HCID 23598686, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing (3-tert-butoxycarbonylamino-2-oxo-2,3,4,7-tetrahydroazepin-1-yl) acetic acid methyl ester, 2, (0.57 g, 2.0 mmol) in 10 mL of CH2Cl2 is treated with 2.5 mL of wet TFA and stirred at room temperature for 30 minutes. The solution is concentrated in vacuo and treated with saturated NaHCO3. Solid NaCl is added to the resulting aqueous solution and the solution is extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated in vacuo to afford the desired intermediate which can be used without further purification.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. additiontreated with saturated NaHCO3
  3. additionSolid NaCl is added to the resulting aqueous solution
  4. extractionthe solution is extracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94d1c0fc45e74ad980cff0545da21eea
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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