Trifluoroacetic acid → HCID 70069385, compound

HRID 1904587Notes

Reaction equation

HRID 1904587 reaction equation
[CH2:1]([C:8](=[CH2:25])[C:9]([NH:11][N:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(Cl)Cl>[CH2:25]=[C:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([NH:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:10]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 53761685HCID 53761685, compound

Product 1

HCID 70069385HCID 70069385, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an inert atmosphere, 7.4 g of the product of Step A were cooled to -15° C. in 20 ml of methylene chloride and then 13 ml of trifluoroacetic acid were added dropwise. After allowing to return to ambient temperature and stirring for 2 hours, neutralizing with a saturated aqueous solution of sodium bicarbonate, extractin was done with ethyl acetate. The extracts were washed with salted water, dried and the solvents were eliminated under reduced pressure to obtain 3.6 g of the expected product melting at 78° C.

Workup

  1. customto return to ambient temperature
  2. washThe extracts were washed with salted water
  3. customdried

Sources & evidence

ORD record
ord-65b907fc0f434a9d98c57a411bafef43
Source dataset
uspto-grants-1989_06
Patent number
US04839358

Reaction notes

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