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Hydrogen Peroxide → (2S,3R)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-(formyloxy)-5-[4-(6-methoxypyridin-3-yl)phenyl]pentanoic acid

HRID 84009
Notes
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Reaction equation

HRID 84009 reaction equation
[CH:1]([O:3][C@H:4]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)=[CH:25][CH:24]=1)[C@@H:5]([CH:19]=[O:20])[CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])=[O:2].P([O-])(O)(O)=[O:38].[Na+].OO.Cl([O-])=O.[Na+]>C(#N)C.O>[O:18]=[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[O:17])[N:8]1[CH2:7][CH2:6][C@@H:5]([C@H:4]([O:3][CH:1]=[O:2])[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)=[CH:27][CH:28]=1)[C:19]([OH:38])=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86700969HCID 86700969, compound

Product 1

HCID 86700970(2S,3R)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-(formyloxy)-5-[4-(6-methoxypyridin-3-yl)phenyl]pentanoic acidYield 221.1%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

The compound obtained in step h (0.54 g) was taken in acetonitrile (6 mL) and water (1 mL). To this solution, sodium dihydrogen phosphate (0.054 g) was added. The reaction mixture was cooled to 0° C. and hydrogen peroxide (1 mL) and sodium chlorite (0.208 g) were added. After stirring the reaction mixture for an additional 1 hour, the solvents were 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 get the title compound (0.5 g).

Workup

  1. customthe solvents were evaporated on a rotary evaporator
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e8129ecd24544c088246d128b46c1b73
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846910B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes