Potassium Carbonate → 1,1-Dimethylethyl N-[(1-ethynylcyclopropyl)sulfonyl]carbamate

HRID 420061

Reaction equation

HRID 420061 reaction equation
[C:1]([NH:8][S:9]([C:12]1([CH:15]=O)[CH2:14][CH2:13]1)(=[O:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17]([O-])([O-])=O.[K+].[K+].C/C(/[O-])=C(/P(OC)(OC)=O)\[N+]#N>CO>[C:1]([NH:8][S:9]([C:12]1([C:15]#[CH:17])[CH2:14][CH2:13]1)(=[O:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 578166791108658-38-3HCID 178502985HCID 178502985, compound

Product 1

HCID 578166891,1-Dimethylethyl N-[(1-ethynylcyclopropyl)sulfonyl]carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of compound 80 (230 mg, 0.92 mmol) in MeOH (5 mL) at 0° C. was added K2CO3 (255 mg, 1.84 mmol), and Ohira-Bestmann reagent (215 g, 1.10 mmol) (Tetr. Lett. 2008, 49, 4454). The mixture was stirred at room temperature for 16 hrs and was concentrated under reduced pressure. Water, EtOAc, and citric acid were added to bring pH to 4-5. Organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 81 in 85% yield.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionWater, EtOAc, and citric acid were added
  3. dry with materialOrganics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50656435da35495c8fb7a297723df239
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Linked notes

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