O-Xylene → HCID 136115984, compound

HRID 1662059Notes

Reaction equation

HRID 1662059 reaction equation
[NH2:1][C:2](=[N:16][O:17][C:18]([O:20]CC(CC)CCCC)=O)[C@@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].C1(C)C(C)=CC=CC=1>C(OCC)(=O)C>[O:20]=[C:18]1[O:17][N:16]=[C:2]([C@@H:3]2[CH2:7][CH2:6][CH2:5][C@@H:4]2[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[NH:1]1

Participants

4

Reactant 2

HCID 7237O-XyleneHCID 86644627HCID 86644627, compound

Product 1

HCID 136115984HCID 136115984, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of tert-butyl [(1S,2R)-2-{amino[({[(2-ethyl hexyl)oxy]carbonyl}oxy)imino]methyl}cyclopentyl]carbamate (492 mg) and xylene (10 ml) was stirred at an outside temperature of 140° C. for 4 hours. The reaction mixture was left to be cooled, ethyl acetate (40 ml) was added, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (1% methanol-chloroform) to obtain tert-butyl [(1S,2R)-2-(5-oxo -4,5-dihydro-1,2,4-oxadiazol-3-yl)cyclopentyl]carbamate (328 mg) as a pale yellow solid.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. washby washing with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was then removed by evaporation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (1% methanol-chloroform)

Sources & evidence

ORD record
ord-d292ffdedb3a4e14b82126ed1078c6b9
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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