Perchloric Acid → 2-(2-{(2R,3R,4S,5R)-2-[2-(3',5'-difluorobiphenyl-4-yl)ethyl]-4,5-dihydroxytetrahydrofuran-3-yl}ethyl)-1H-isoindole-1,3(2H)-dione

HRID 84012Notes

Reaction equation

HRID 84012 reaction equation
Cl(O)(=O)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C@H:22]3[O:31][C@H:25]4[O:26]C(C)(C)[O:28][C@H:24]4[C@H:23]3[CH2:32][CH2:33][N:34]3[C:42](=[O:43])[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:35]3=[O:44])=[CH:16][CH:15]=2)[CH:10]=[C:11]([F:13])[CH:12]=1>C(#N)C.C(OCC)(=O)C.O>[F:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C@@H:22]3[C@H:23]([CH2:32][CH2:33][N:34]4[C:35](=[O:44])[C:36]5[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:42]4=[O:43])[C@H:24]([OH:28])[C@H:25]([OH:26])[O:31]3)=[CH:16][CH:15]=2)[CH:10]=[C:11]([F:13])[CH:12]=1

Participants

6

Reactant 2

HCID 24247Perchloric AcidHCID 67182644HCID 67182644, compound

Product 1

HCID 671820202-(2-{(2R,3R,4S,5R)-2-[2-(3',5'-difluorobiphenyl-4-yl)ethyl]-4,5-dihydroxytetrahydrofuran-3-yl}ethyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

Perchloric acid (0.3 mL) was added to a solution of the compound obtained from step b above (0.2 g) in acetonitrile (6 mL) and water (2 mL) at room temperature. The reaction mixture was heated to 55° C. for 30 minutes. The reaction mixture was then quenched using sodium bicarbonate solution. The solvents were evaporated under reduced pressure. The residue thus obtained was taken up in ethyl acetate and water. The organic layer was separated and washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was concentrated under reduced pressure to yield the title compound (0.15 g).

Workup

  1. customat room temperature
  2. customThe reaction mixture was then quenched
  3. customThe solvents were evaporated under reduced pressure
  4. customThe residue thus obtained
  5. customThe organic layer was separated
  6. washwashed with water and brine solution
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93ef99fa134c49a394c9702f5773f344
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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