Trifluoroacetic acid → HCID 58136644, compound

HRID 877244Notes

Reaction equation

HRID 877244 reaction equation
[CH:1]1([CH:6]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:29](=O)[C:28]4[C:23](=[C:24]([F:32])[CH:25]=[CH:26][C:27]=4[F:31])[CH:22]3[OH:33])=[CH:16][CH:15]=2)[C:7]([O:9]C(C)(C)C)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH:1]1([CH:6]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][N:21]3[CH2:29][C:28]4[C:23](=[C:24]([F:32])[CH:25]=[CH:26][C:27]=4[F:31])[C:22]3=[O:33])=[CH:18][CH:19]=2)[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58136752HCID 58136752, compound

Product 1

HCID 58136644HCID 58136644, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90.0 mg (0.20 mmol) of tert-butyl cyclopentyl{4-[(4,7-difluoro-1-hydroxy-3-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate were initially charged in 1 ml of dichloromethane, and 300 μA of trifluoroacetic acid and 62 μl (0.39 mmol) of triethylsilane were added. The mixture was stirred at RT for 2 h. The reaction mixture was then concentrated on a rotary evaporator, the residue was taken up in ethyl acetate and the solution was washed with water and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. This gave 77.0 mg of the target compound.

Workup

  1. concentrationThe reaction mixture was then concentrated on a rotary evaporator
  2. washthe solution was washed with water and saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58d84bc8b8564146982e498c1bcd51be
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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