18-Crown-6 → HCID 86731685, compound

HRID 1504801Notes

Reaction equation

HRID 1504801 reaction equation
CC1C=CC(S(O[CH2:12][C:13]2([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:14]2)(=O)=O)=CC=1.C1OCCOCCOCCOCCOCCOC1.[K].[C:43]1(=[O:53])[NH:47][C:46](=[O:48])[C:45]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]12>CN(C=O)C>[O:48]=[C:46]1[C:45]2[C:44](=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:43](=[O:53])[N:47]1[CH2:12][C:13]1([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 24194345Phthalimide potassium saltHCID 86731683Carbamic acid, N-[1-[[[(4-methylphenyl)sulfonyl]oxy]methyl]cyclopropyl]-, 1,1-dimethylethyl ester

Product 1

HCID 86731685HCID 86731685, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of {1-[(tert-butoxycarbonyl)amino]cyclopropyl}methyl 4-methylbenzenesulfonate (100 g, 293 mmol) in DMF (1000 mL) was added 18-crown-6 (76.8 g, 291 mmol) and phthalimide potassium salt (80.5 g, 435 mmol). The reaction mixture was heated to 50° C. After 3 hours, the reaction mixture was cooled to ambient temperature, quenched with cold water (2000 mL), and filtered to afford crude solids. The solids were washed with petroleum ether (3×200 mL) and dried under reduced pressure to afford tert-butyl {1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]cyclopropyl}carbamate. The material was used without further purification.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. customquenched with cold water (2000 mL)
  3. filtrationfiltered
  4. customto afford crude solids
  5. washThe solids were washed with petroleum ether (3×200 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-9bed6614970f408a809629634d1c1995
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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