Trifluoroacetic acid → HCID 15463356, compound

HRID 1636883Notes

Reaction equation

HRID 1636883 reaction equation
[C:1]1([C:7]([NH:9][C:10]2[S:11][C:12]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:13]([CH3:22])[C:14]=2[C:15]([O:17]C(C)(C)C)=[O:16])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:26]([O:25][C:23]([C:12]1[S:11][C:10]([NH:9][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:8])=[C:14]([C:15]([OH:17])=[O:16])[C:13]=1[CH3:22])=[O:24])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15463354HCID 15463354, compound

Product 1

HCID 15463356HCID 15463356, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound prepared in Example 8 (1.33 g, 2.94 mmol) in DCM (20 ml). was added TFA (20 ml) dropwise. After 19 hours, the reaction was concentrated under reduced pressure, and partitioned between CHCl3 and H2O. The aqueous phase basified with sat. NaHCO3, and the layers were separated. The aqueous phase was extracted with CHCl3. The combined organic layers were washed with H2O, dried over MgSO4 and concentrated under reduced pressure to yield 1.10 g (95%) of a tan solid. 1H-NMR (CDCl3) 2.76 (s, 3H) 5.23 (s, 2H), 7.20-7.60 (m, 8H), 7.93 (d, 2H, J=8.0 Hz)

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. custompartitioned between CHCl3 and H2O
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with CHCl3
  5. washThe combined organic layers were washed with H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2db774232ea94ef9a653094f593b8494
Source dataset
uspto-grants-2000_03
Patent number
US06037340

Reaction notes

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