Cyanuric chloride → HCID 68358959, compound

HRID 1408976Notes

Reaction equation

HRID 1408976 reaction equation
[C:1]([C@@:4]1([CH3:15])[CH2:8][CH2:7][C@@H:6]([C:9]([O:11][CH3:12])=[O:10])[C:5]1([CH3:14])[CH3:13])(=O)[NH2:2].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[C:1]([C@@:4]1([CH3:15])[CH2:8][CH2:7][C@@H:6]([C:9]([O:11][CH3:12])=[O:10])[C:5]1([CH3:14])[CH3:13])#[N:2]

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 36690158HCID 36690158, compound

Product 1

HCID 68358959HCID 68358959, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1R,3S)-methyl 3-carbamoyl-2,2,3-trimethylcyclopentane carboxylate (4.49 g, 21.05 mmol) in DMF (35 ml) at room temperature was added cyanuric chloride (2.329 g, 12.63 mmol). The reaction mixture was stirred for 14 hrs. The reaction solution was partitioned between water and ethyl acetate. The ethyl acetate extracts were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure, yielding (1R,3S)-methyl 3-cyano-2,2,3-trimethylcyclopentanecarboxylate (3.73 g, 19.10 mmol, 91% yield) as a white solid. ESI-MS m/z 218.2 ([M+H]+).

Workup

  1. customThe reaction solution was partitioned between water and ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5c2be31697c45dcba446b20a8d33df1
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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