Trifluoroacetic acid → HCID 61717606, compound

HRID 1400949Notes

Reaction equation

HRID 1400949 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)[CH3:7])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:8]1([CH:6]([CH3:7])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67443686HCID 67443686, compound

Product 1

HCID 61717606HCID 61717606, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 513 (1.02 g, 3.40 mmol) and TFA (10 ml) in DCM (50 ml) was stirred at rt for 3 h. The reaction mixture was concentrated (azeotropes with DCM), diluted in water, and the pH was adjusted to around 8-9 with a saturated aqueous solution of sodium bicarbonate and 1N NaOH, and extracted with DCM. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to afford the desired product 514 (411 mg, 2.05 mmol, 60% yield) as a yellow sticky oil that was used crude in the next step without any further purification. MS (m/z): 201.3 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated (azeotropes with DCM)
  2. additiondiluted in water
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6654cedc2ccf4b7383a458e43e538cf5
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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