Benzoic Acid → N-t-butyl-3-benzoyloxy-1-pentanesulfonamide

HRID 2229457Notes

Reaction equation

HRID 2229457 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([NH:14][S:15]([CH2:18][CH2:19][CH:20](O)[CH2:21][CH3:22])(=[O:17])=[O:16])([CH3:13])([CH3:12])[CH3:11].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O1CCCC1>[C:10]([NH:14][S:15]([CH2:18][CH2:19][CH:20]([O:8][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:21][CH3:22])(=[O:17])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 18467556N-t-butyl-3-hydroxy-1-pentanesulfonamideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18467574N-t-butyl-3-benzoyloxy-1-pentanesulfonamideYield 104.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, N,N′-carbonyldiimidazole (90.0 g) was added to a solution of benzoic acid (67.7 g) in tetrahydrofuran (400 ml) in an ice bath and the solution was stirred for 1 hour at room temperature. N-t-butyl-3-hydroxy-1-pentanesulfonamide (59.0 g) was added thereto at room temperature. Subsequently, diazabicycloundecene (84.5 g) was added thereto in an ice bath. The mixture was stirred overnight at room temperature. About ½ volume of tetrahydrofuran was removed under reduced pressure. The reaction solution was made acidic with dilute hydrochloric acid in an ice bath and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate. Deposited solid was separated by filtration. After washing the organic layer with saturated brine and drying it over sodium sulfate, the solvent was removed under reduced pressure to obtain N-t-butyl-3-benzoyloxy-1-pentanesulfonamide (90.42 g) as oil.

Workup

  1. customat room temperature
  2. stirringThe mixture was stirred overnight at room temperature
  3. customAbout ½ volume of tetrahydrofuran was removed under reduced pressure
  4. customThe reaction solution was made acidic with dilute hydrochloric acid in an ice bath
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate
  7. customDeposited solid was separated by filtration
  8. washAfter washing the organic layer with saturated brine
  9. dry with materialdrying it over sodium sulfate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-06112c47341b4975b33f495e5f28f5c2
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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