Water → HCID 58345210, compound

HRID 624275Notes

Reaction equation

HRID 624275 reaction equation
[CH3:1][C:2]([CH3:21])([S:4]([NH:6][C:7]1([C:11]2[CH:16]=[CH:15][C:14]([NH:17]C(=O)C)=[CH:13][CH:12]=2)[CH2:10][O:9][CH2:8]1)=[O:5])[CH3:3].O>C(OCC)(=O)C>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:7]2([NH:6][S:4]([C:2]([CH3:21])([CH3:3])[CH3:1])=[O:5])[CH2:8][O:9][CH2:10]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 962WaterHCID 68754025HCID 68754025, compound

Product 1

HCID 58345210HCID 58345210, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Claisen's alkali (potassium hydroxide, 12.7 g in 9 ml water and 33 ml methanol) was added to N-(4-(3-(1,1-dimethylethylsulfinamido)oxetan-3-yl)phenyl)acetamide (300 mg, 0.966 mmol) and the reaction was stirred at 90° C. for 2 hours. The mixture was cooled to room temperature when water and ethyl acetate were added. The aqueous layer was extracted twice with ethyl acetate and the combined organics were dried with magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by regular phase flash column chromatography to give the title compound.

Workup

  1. additionwere added
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialthe combined organics were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by regular phase flash column chromatography

Sources & evidence

ORD record
ord-b3055091c0c7453697ff4101db31528f
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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