Hydrogen Peroxide → HCID 801657, compound

HRID 1907155Notes

Reaction equation

HRID 1907155 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@H:12]([CH2:16][CH2:17][S:18][CH3:19])[C:13]([OH:15])=[O:14].[OH:20]O>CO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@H:12]([CH2:16][CH2:17][S:18]([CH3:19])=[O:20])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 1551691HCID 1551691, compound

Product 1

HCID 801657HCID 801657, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of (R)-2-(1,3-dioxoisoindolin-2-yl)-4-(methylthio)butanoic acid (87.124 g, 312 mmol) from preparation 54 in methanol (750 ml) was added hydrogen peroxide (pre-cooled to −30° C.; 38.9 g, 343 mmol) in methanol (250 ml) at −20° C. The reaction mixture was stirred at −20° C. overnight (by use of a cryostat) then warmed to rt over a further 24 hours then to 30° C. for 5 h, LCMS suggesting 95% conversion. The reaction mixture was evaporated under vacuum to give the title compound as a mixture of diastereoisomers that were progressed directly in preparation 3.

Workup

  1. temperaturethen warmed to rt over a further 24 hours
  2. waitto 30° C. for 5 h
  3. customThe reaction mixture was evaporated under vacuum

Sources & evidence

ORD record
ord-35f489a6c1894ebead06274d898e2336
Source dataset
uspto-grants-2013_12
Patent number
US08598123B2

Reaction notes

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