Hydrochloric Acid → HCID 58207628, compound

HRID 1026836Notes

Reaction equation

HRID 1026836 reaction equation
[CH:1]1([S:4]([NH2:7])(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>CC(C)=O.O>[CH:1]1([S:4]([NH:7][C:15](=[O:16])[O:17][CH2:18][CH3:19])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 15765418Cyclopropanesulfonamide

Product 1

HCID 58207628HCID 58207628, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of cyclopropanesulfonamide (Li, J. et al; Synlett 2006, 5, 725-728) (800 mg, 6.60 mmol) in acetone (25 ml) was added potassium carbonate (2.738 g, 3 eq, 19.81 mmol) and ethyl chloroformate (1.075 g, 1.5 eq, 9.90 mmol) and the reaction mixture was stirred at RT overnight. The reaction mixture was poured into water and made acidic (pH 1) with cone HCl then extracted with EtOAc. The extract was collected, dried over Na2SO4, filtered and concentrated. Purification of the residue by column chromatography (eluent 30% EtOAc in hexanes) afforded 374 as a colourless oil (800 mg, 63%). 1H NMR (DMSO, d6) 11.47 (s, 1H), 4.10 (q, J=10.27 Hz, 2H), 2.90 (m, 1H), 1.19 (t, J=7.24 Hz, 3H), 1.039 (m, 4H).

Workup

  1. extractionthen extracted with EtOAc
  2. customThe extract was collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by column chromatography (eluent 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3638c512bf464581a7e441f10e4a0ebf
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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