4-Toluenesulfonyl chloride → 2-Tert-butoxycarbonylamino-2-methyl-1-propyl p-toluenesulfonate

HRID 354492Notes

Reaction equation

HRID 354492 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CCOCC>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([O:11][CH2:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([CH3:13])[CH3:12])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 235119882-Tert-butoxycarbonylamino-2-methyl-1-propyl p-toluenesulfonateYield 82.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of 2-tert-butoxycarbonylamino-2-methyl-1-propanol (5.7 g, 30.11 mmol) and powdered NaOH (6.7 g, 0.151 mol) in Et2O (200 mL) was added p-toluenesulfonyl chloride (6.9 g, 36.14 mmol) at room temp. The stirred resulting mixture was heated under reflux for 8 hr. After cooling, ice-water (100 mL) was added to the solution. Separated Et2O layer was washed with brine, dried over Na2SO4, and evaporated. To the residue was added n-hexane and triturated. The solid was collected to afford 8.5 g (82.2%) 2-tert-butoxycarbonylamino-2-methyl-1-propyl p-toluenesulfonate as a crystalline material. 1H-NMR (CDCl3) δ1.26 (s, 6H), 1.38 (s, 9 H), 2.37 (s, 3H), 4.05 (s, 2H), 4.49 (br, 1H), 7.34 (d, J=7.8 Hz, 2H), 7.78 (d, J=7.8 Hz, 2H).

Workup

  1. customThe stirred resulting mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 8 hr
  4. temperatureAfter cooling
  5. washSeparated Et2O layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. additionTo the residue was added n-hexane
  9. customtriturated
  10. customThe solid was collected

Sources & evidence

ORD record
ord-8decdc043ac34ed2bd7d630bd19197f2
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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