4-Toluenesulfonyl chloride → Tert-butyl (3-tosyl-cyclobutyl)-carbamate

HRID 2112093Notes

Reaction equation

HRID 2112093 reaction equation
O[CH:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1.C(N(CC)CC)C.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C(Cl)(Cl)Cl>[S:21]([CH:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22594430tert-Butyl (3-hydroxycyclobutyl)carbamate

Product 1

HCID 86606183Tert-butyl (3-tosyl-cyclobutyl)-carbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

18.7 g (100 mmol) tert.butyl (3-hydroxy-cyclobutyl)-carbamate and 12.1 g (120 mmol) triethylamine are placed in 500 ml chloroform. 20.5 g (105 mmol) tosyl chloride, dissolved in 150 ml chloroform, is added dropwise to this solution at 0° C. with stirring. Then the mixture is left to come up to ambient temperature and stirred for 2 h. The organic phase is washed successively with water, dilute hydrochloric acid, sodium hydrogen carbonate solution and water. The organic phase is dried with magnesium sulphate and the solvent is eliminated in vacuo.

Workup

  1. additionis added dropwise to this solution at 0° C.
  2. waitThen the mixture is left
  3. customto come up to ambient temperature
  4. stirringstirred for 2 h
  5. washThe organic phase is washed successively with water, dilute hydrochloric acid, sodium hydrogen carbonate solution and water
  6. dry with materialThe organic phase is dried with magnesium sulphate

Sources & evidence

ORD record
ord-772b9e55fe9a428abf4d39157259cee8
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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