Trifluoroacetic acid → HCID 178441295, compound

HRID 76286

Reaction equation

HRID 76286 reaction equation
[CH2:1]([C:5]1=[CH:6][N:7]([C:25]([CH3:28])([CH3:27])[CH3:26])[S:8]/[C:9]/1=[N:10]\[C:11]([CH:13]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1)=[O:12])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([C:5]1=[CH:6][N:7]([C:25]([CH3:26])([CH3:28])[CH3:27])[S:8]/[C:9]/1=[N:10]\[C:11]([CH:13]1[CH2:17][CH2:16][NH:15][CH2:14]1)=[O:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 178441299HCID 178441299, compound

Product 1

HCID 178441295HCID 178441295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20-mL scintillation vial containing a magnetic stir bar were added the product from Example 104A (143 mg, 0.350 mmol), anhydrous dichloromethane (5 mL), and trifluoroacetic acid (200 mg, 1.75 mmol). The pale yellow solution was stirred at room temperature for 4 hours. The pH of the reaction mixture was adjusted to ˜9 by addition of saturated aqueous sodium bicarbonate solution. The mixture was extracted with dichloromethane (3×10 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated by rotary evaporator to afford the title compound. The crude product was used without purification for the next step. MS (ESI+) m/z 310 (M+H)+.

Workup

  1. additionTo a 20-mL scintillation vial containing a magnetic stir bar
  2. extractionThe mixture was extracted with dichloromethane (3×10 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-ffa3e5b5e91d4e3ca341b5517ad8b2ff
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Linked notes

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