Dimethylformamide → HCID 59454078, compound

HRID 1662050Notes

Reaction equation

HRID 1662050 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=O)[NH2:2].CN(C=O)C.ClC1N=C(Cl)N=C(Cl)N=1>C(OCC)(=O)C>[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 12051857HCID 12051857, compound

Product 1

HCID 59454078HCID 59454078, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl [(1S,2R)-2-carbamoylcyclopentyl]carbamate (500 mg) and DMF (5.0 ml) was ice-cooled, and 2,4,6-trichloro-1,3,5-triazine (404 mg) was added thereto, followed by stirring under ice-cooling for 1 hour, and further at room temperature for 2 hours. To the reaction mixture were added ethyl acetate and a saturated sodium bicarbonate solution, and then liquid-separation was carried out. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to obtain tert-butyl [(1S,2R)-2-cyanocyclopentyl]carbamate (430 mg) as a white solid.

Workup

  1. temperaturecooled
  2. temperaturecooling for 1 hour
  3. customa saturated sodium bicarbonate solution, and then liquid-separation
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-37989ca1e3ee4fedaea81f5154323f89
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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