N-Hydroxysuccinimide → 1-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanoate

HRID 1669903Notes

Reaction equation

HRID 1669903 reaction equation
[CH3:1][CH:2]([CH3:24])[C:3]([O:5][CH:6]([O:10][C:11]([O:13]C1C=CC(S(C)(=O)=O)=CC=1)=[O:12])[CH:7]([CH3:9])[CH3:8])=[O:4].O[N:26]1[C:30](=[O:31])[CH2:29][CH2:28][C:27]1=[O:32]>ClCCl>[CH3:24][CH:2]([CH3:1])[C:3]([O:5][CH:6]([O:10][C:11]([O:13][N:26]1[C:30](=[O:31])[CH2:29][CH2:28][C:27]1=[O:32])=[O:12])[CH:7]([CH3:8])[CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 80170N-HydroxysuccinimideHCID 592705152-Methyl-1-[4-(methylsulfonyl)phenoxycarbonyloxy]propyl 2-methylpropanoate

Product 1

HCID 448146361-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-1-[4-(methylsulfonyl)phenoxycarbonyloxy]propyl 2-methylpropanoate D6 is dissolved in dichloromethane at a concentration of 10% (w/vol). N-hydroxysuccinimide (1.1 equivalents) is added to the solution. The reaction mixture is warmed to reflux and stirred until the reaction is complete. The organic phase is extracted twice with a 10% potassium carbonate solution followed by a wash with water (2×). Drying over sodium sulfate is followed by solvent evaporation to provide the title compound E2.

Workup

  1. temperatureThe reaction mixture is warmed
  2. temperatureto reflux
  3. extractionThe organic phase is extracted twice with a 10% potassium carbonate solution
  4. washa wash with water (2×)
  5. dry with materialDrying over sodium sulfate
  6. customis followed by solvent evaporation

Sources & evidence

ORD record
ord-1883974aad084c9ebf9249cb649d5e1c
Source dataset
uspto-grants-2011_08
Patent number
US07989641B2

Reaction notes

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