Water → HCID 23061768, compound

HRID 1844849Notes

Reaction equation

HRID 1844849 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C1C=C(Cl)C=C(C(OO)=[O:21])C=1.[OH2:24].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][S:2]([CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])(=[O:21])=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 4145154Tert-Butyl (2-(methylthio)ethyl)carbamate

Product 1

HCID 23061768HCID 23061768, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a dried reaction flask, the crude tert-butyl 2-(methylthio)ethylcarbamate (2.464 g, about 11.0 mmol) was dissolved in tetrahydrofuran (22 mL). To the mixture was added 77% mCPBA (5.698 g, 25.42 mmol) in portion at 0° C. The mixture was stirred for 1 hr. Water, saturated aqueous sodium bicarbonate solution and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with saturated salt water, dried over anhydrous sodium sulfate, and was purified by silica gel column chromatography with ethyl acetate to obtain a white solid (0.95 g) in 38.7% yield.

Workup

  1. customIn a dried reaction flask
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic phase was washed with saturated salt water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customwas purified by silica gel column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-e3e94b9ffb1b4046a71119e985e973f1
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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