Methyl N-(triethylammoniosulfonyl)carbamate → HCID 59541900, compound

HRID 1893226Notes

Reaction equation

HRID 1893226 reaction equation
O[C:2]1([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15](=[O:17])[NH:14][C:13]=3[CH:18]=2)[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[O:8]=[C:5]1[CH2:6][CH2:7][C:2]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15](=[O:17])[NH:14][C:13]=3[CH:18]=2)=[CH:3][CH2:4]1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59541926HCID 59541926, compound

Product 1

HCID 59541900HCID 59541900, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(1-hydroxy-4-oxo-cyclohexyl)-3H-benzooxazol-2-one (230 mg, 0.93 mmol) in THF (10 mL) was treated with Burgess' reagent (Aldrich, 334 mg, 1.40 mmol) at room temperature. The reaction was stirred overnight. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated and then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-c425bd4a23c74889b6103b9666f7d44e
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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