Trifluoroacetic acid → 2-(2-{(2R,3S,4R,5S)-2-[2-(4'-chlorobiphenyl-4-yl)ethyl]-4,5-dihydroxytetrahydrofuran-3-yl}ethyl)-1H-isoindole-1,3(2H)-dione

HRID 2410440Notes

Reaction equation

HRID 2410440 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C@H:23]3[O:32][C@@H:26]4[O:27]C(C)(C)[O:29][C@@H:25]4[C@@H:24]3[CH2:33][CH2:34][N:35]3[C:43](=[O:44])[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:36]3=[O:45])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>C(OCC)(=O)C.O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C@@H:23]3[C@@H:24]([CH2:33][CH2:34][N:35]4[C:36](=[O:45])[C:37]5[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=5)[C:43]4=[O:44])[C@@H:25]([OH:29])[C@@H:26]([OH:27])[O:32]3)=[CH:19][CH:20]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67182870HCID 67182870, compound

Product 1

HCID 671824032-(2-{(2R,3S,4R,5S)-2-[2-(4'-chlorobiphenyl-4-yl)ethyl]-4,5-dihydroxytetrahydrofuran-3-yl}ethyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid (1 mL) and water (0.5 mL) were added to the compound obtained from step k above (0.04 g). The reaction mixture was stirred at room temperature for 2 hours. The solvents were evaporated at reduced pressure. The residue thus obtained was taken in ethyl acetate and water. The organic layer was separated, washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was concentrated under reduced pressure to yield the title compound (0.028 g).

Workup

  1. customThe solvents were evaporated at reduced pressure
  2. customThe residue thus obtained
  3. customThe organic layer was separated
  4. washwashed with water and brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f1d12bea33e0498897844616ce06dab6
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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