1,1-Dimethylethyl N-[1-[2-[(methylsulfonyl)oxy]ethyl]cyclopropyl]carbamate → HCID 12993141, compound

HRID 1786162Notes

Reaction equation

HRID 1786162 reaction equation
CS(O[CH2:6][CH2:7][C:8]1([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:9]1)(=O)=O.[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[K]>CN(C)C=O>[O:24]=[C:22]1[C:21]2[C:20](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19](=[O:29])[N:23]1[CH2:6][CH2:7][C:8]1([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 129931401,1-Dimethylethyl N-[1-[2-[(methylsulfonyl)oxy]ethyl]cyclopropyl]carbamateHCID 24194345Phthalimide potassium salt

Product 1

HCID 12993141HCID 12993141, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 7.82 g (28 mmol) of 2-{1-[(tert-butoxycarbonyl)amino]-cyclopropyl}ethyl methanesulfonate in 35 ml of anhydrous dimethylformamide was added 5.45 g (29.4 mmol) of potassium phthalimide. The resulting mixture was stirred at 150° C. for 18 h. The mixture was then filtered and washed with diethyl ether. The filtrate was evaporated to dryness, the crude product was heated in water and the precipitate was filtered. The product was dried to give 4.63 g of pure compound as an orange solid. Mp: 125-127° C.

Workup

  1. filtrationThe mixture was then filtered
  2. washwashed with diethyl ether
  3. customThe filtrate was evaporated to dryness
  4. temperaturethe crude product was heated in water
  5. filtrationthe precipitate was filtered
  6. customThe product was dried

Sources & evidence

ORD record
ord-6b11e0e4e9fa49aabf72bc36725928b3
Source dataset
uspto-grants-2009_03
Patent number
US07507743B2

Reaction notes

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