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2-{1-[(Tert-butoxycarbonyl)amino]cyclopropyl}ethyl methanesulfonate → HCID 12993141, compound

HRID 539967
Notes
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Reaction equation

HRID 539967 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])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:28])[NH:20]1.[K]>CN(C)C=O>[O:29]=[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](=[O:28])[N:20]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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 129931402-{1-[(Tert-butoxycarbonyl)amino]cyclopropyl}ethyl methanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 12993141HCID 12993141, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-{1-[(tert-butoxycarbonyl)amino]-cyclopropyl}ethyl methanesulfonate (9.5 g, 344.3 mmol) in anhydrous N,N-dimethylformamide (20 ml) was added potassium 2,3-dihydro-1H-isoindole-1,3-dione (7.0 g, 37 mmol). After being stirred at 150° C. for 18 hours, the resulting mixture was then filtered and washed with diethyl ether (50 mL). The filtrate was washed with brine (50 mL×3), dried over sodium sulfate and concentrated in vacuo. The residue was heated with stirring in water and the precipitate was collected by filtration and dried in vacuo to afford 6.0 g of the pure product as an orange solid (yield was 53%).

Workup

  1. filtrationthe resulting mixture was then filtered
  2. washwashed with diethyl ether (50 mL)
  3. washThe filtrate was washed with brine (50 mL×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. temperatureThe residue was heated
  7. stirringwith stirring in water
  8. filtrationthe precipitate was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-acb793fb3ad64145903c0225ba902c42
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871756B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes