Dichloromethane → Diisopropyl Ether

HRID 1374096Notes

Reaction equation

HRID 1374096 reaction equation
CS(O[CH:6]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=O)=O.[OH-].[Na+].[CH2:28](Cl)Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH:18]([O:17][CH:16]([CH3:6])[CH3:28])([CH3:19])[CH3:23].[C:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH:6]2[CH2:7][N:8]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:19][CH:20]=1)#[N:25]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 218675772-[(tert-Butoxycarbonyl)amino]-1-[(4-cyanophenoxy)methyl]ethyl methanesulfonate

Product 2

HCID 7914Diisopropyl EtherHCID 21867670Tert-butyl 2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

A cooled (0° C.) solution of 2-[(tert-butoxycarbonyl)amino]-1-[(4-cyanophenoxy)methyl]ethyl methanesulfonate (from step (iv) above; 30.6 g, 82.6 mmol) and tetrabutylammonium hydrogensulfate (3 g, 8.8 mmol) in DCM (100 mL) was treated with 50 wt. % aqueous NaOH (60 mL) under an inert atmosphere. The resulting mixture was stirred, and the temperature was slowly allowed to rise to rt over for 4 h, and then extracted with ether. The organic layer was washed with water and concentrated in vacuo to give a residue that was purified by column chromatography (dichloromethane eluent). Crystallisation from diethyl ether:di-iso-propyl ether gave the sub-title compound in quantitative yield.

Workup

  1. customto rise to rt over for 4 h
  2. extractionextracted with ether
  3. washThe organic layer was washed with water
  4. concentrationconcentrated in vacuo
  5. customto give a residue that
  6. customwas purified by column chromatography (dichloromethane eluent)
  7. customCrystallisation from diethyl ether

Sources & evidence

ORD record
ord-566a931109544ca1997e16d17200568f
Source dataset
uspto-grants-2007_01
Patent number
US07164017B2

Reaction notes

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