Trifluoroacetic acid → HCID 56945608, compound

HRID 1474564Notes

Reaction equation

HRID 1474564 reaction equation
[Br:1][CH2:2][C:3](=[CH2:32])[C:4]([N:6]([CH:18]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:19]([NH:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:20])CC1C=CC(OC)=CC=1OC)=[O:5].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:1][CH2:2][C:3](=[CH2:32])[C:4]([NH:6][CH:18]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:19]([NH:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:20])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 56945724HCID 56945724, compound

Product 1

HCID 56945608HCID 56945608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 1 (117 mg, 0.23 mmol) was dissolved in methylene chloride (2 ml). Next, this was supplemented with trifluoroacetic acid (475 μl) at room temperature. The mixture was left for 1 hour while observing the colour change from clear to dark violet. The flask contents were transferred into a separator, and this was supplemented with methylene chloride (4 ml) and a saturated solution of sodium carbonate was added until the disappearance of the violet colour. The aqueous phase was extracted with methylene chloride (3×8 ml), and then the combined organic phases were dried with brine and the solvent was evaporated off. The remainder was purified using column chromatography in a hexane: ethyl acetate system (silica gel, Rf=0.25, 6:4, v:v).

Workup

  1. extractionThe aqueous phase was extracted with methylene chloride (3×8 ml)
  2. dry with materialthe combined organic phases were dried with brine
  3. customthe solvent was evaporated off
  4. customThe remainder was purified

Sources & evidence

ORD record
ord-4d4986876467491aa764de10f9a0245b
Source dataset
uspto-grants-2015_04
Patent number
US09018255B2

Reaction notes

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