Sodium periodate → (1R,2S)-1-[2-(3',5'-difluorobiphenyl-4-yl)ethyl]-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-formylbutyl formate

HRID 2410423Notes

Reaction equation

HRID 2410423 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C@@H:17]3[C@H:21]([CH2:22][CH2:23][N:24]4[C:32](=[O:33])[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:25]4=[O:34])[C@H:20]([OH:35])[C@H:19]([OH:36])[O:18]3)=[CH:11][CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.I([O-])(=O)(=O)=O.[Na+]>CO>[CH:19]([O:18][C@H:17]([CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=2)=[CH:14][CH:13]=1)[C@@H:21]([CH:20]=[O:35])[CH2:22][CH2:23][N:24]1[C:25](=[O:34])[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]1=[O:33])=[O:36]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 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

Product 1

HCID 86640489(1R,2S)-1-[2-(3',5'-difluorobiphenyl-4-yl)ethyl]-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-formylbutyl formate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound obtained from step c above (0.15 g) in methanol (6 mL) at 0° C., a solution of sodium metaperiodate (0.15 g in 1 mL of water) was added. The reaction mixture was stirred for 2 hours at the same temperature. After stirring the reaction mixture for an additional 1 hour at room temperature, the reaction mixture was evaporated on a rotary evaporator. The residue was taken into water and extracted with ethyl acetate. The organic layer was washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to obtain the title compound (0.12 g).

Workup

  1. stirringAfter stirring the reaction mixture for an additional 1 hour at room temperature
  2. customthe reaction mixture was evaporated on a rotary evaporator
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-91267019fde748759dc9794384c12ac4
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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