HCID 18467561, compound → HCID 18467531, compound

HRID 2229455Notes

Reaction equation

HRID 2229455 reaction equation
C([NH:5][S:6]([CH2:9][CH2:10][CH2:11][CH:12]([O:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:13])(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:15]([O:14][CH:12]([CH3:13])[CH2:11][CH2:10][CH2:9][S:6]([NH2:5])(=[O:8])=[O:7])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 18467561HCID 18467561, compound

Product 1

HCID 18467531HCID 18467531, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of N-t-butyl-4-benzoyloxy-1-pentanesulfonamide (15.0 g) and trifluoroacetic acid (70 ml) was stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure. Water and chloroform were added to the residue. Then, a saturated aqueous solution of sodium hydrogencarbonate was added thereto while stirring to adjust the pH of the aqueous to neutral. The chloroform layer was dried over sodium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography (eluate: ethyl acetate) to obtain 4-benzoyloxy-1-pentanesulfonamide (11.1 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionWater and chloroform were added to the residue
  3. additionThen, a saturated aqueous solution of sodium hydrogencarbonate was added
  4. stirringwhile stirring
  5. dry with materialThe chloroform layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel column chromatography (eluate: ethyl acetate)

Sources & evidence

ORD record
ord-caa27df2319c4765b6e8fd2f70e75afd
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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