Hydrogen Peroxide → HCID 68461883, compound

HRID 501889Notes

Reaction equation

HRID 501889 reaction equation
[C:1]([S:5][CH2:6][C@@:7]1([CH3:14])[NH:11][C:10](=[O:12])[NH:9][C:8]1=[O:13])([CH3:4])([CH3:3])[CH3:2].CO.S(=O)(=O)(O)[OH:18].C(O)(C)C.OO.O>[Cl-].[Na+]>[C:1]([S:5]([CH2:6][C@@:7]1([CH3:14])[NH:11][C:10](=[O:12])[NH:9][C:8]1=[O:13])=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 6

HCID 784Hydrogen Peroxide2×HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 16679761HCID 16679761, compound

Product 1

HCID 68461883HCID 68461883, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Procedure

(5S)-5-[(Tert-butylthio)methyl]-5-methylimidazolidine-2,4-dione (1.00 eq, 46.2 mmol, 10.0 g) was charged to a vessel followed by methanol (2.64 mol, 107 mL, 84.5 g). The resulting clear solution was stirred and a solution of sulfuric acid, 4.40% w/w in iso-propanol (6.22 mmol, 13.9 mL, 13.9 g) was added. To this mixture was then added a solution of hydrogen peroxide, 11.68M, 35% w/w in water (107 mmol, 9.13 mL, 10.4 g) in one portion without external cooling (an exotherm from 22° C. to 41° C. over 10 min was noted). Hplc analysis of the reaction mixture approximately 1.5 h after the addition of the hydrogen peroxide revealed complete consumption of the starting material and the appearance of two new peaks (diastereoisomeric sulfoxides). The mixture was diluted with saturated aqueous sodium chloride solution (231 mL) and extracted with dichloromethane (2×250 mL). The combined organic phases were extracted with water (2×200 mL). The aqueous phase was evaporated to dryness under reduced pressure (water bath temperature 40° C.) to give (5S)-5-[(tert-butylsulfinyl)methyl]-5-methylimidazolidine-2,4-dione as white crystals (0.497 eq, 23.0 mmol, 5.34 g) in 50% yield as a 71:29 mixture of diastereoisomers (by comparison of 1H NMR integrals).

Workup

  1. temperaturewithout external cooling (an exotherm from 22° C. to 41° C. over 10 min
  2. extractionextracted with dichloromethane (2×250 mL)
  3. extractionThe combined organic phases were extracted with water (2×200 mL)
  4. customThe aqueous phase was evaporated to dryness under reduced pressure (water bath temperature 40° C.)

Sources & evidence

ORD record
ord-1480e9feb08b4b338a3dc7717cf6de59
Source dataset
uspto-grants-2010_08
Patent number
US07772403B2

Reaction notes

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