Potassium Carbonate → HCID 86722963, compound

HRID 1404359Notes

Reaction equation

HRID 1404359 reaction equation
[C:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(#N)C.CN(C=O)C.C(OCC)(=O)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][NH:15][CH:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:14][CH2:13]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 178419079HCID 178419079, compound

Product 1

HCID 86722963HCID 86722963, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of trans-N-Boc-1,4-diaminocyclohexane (0.256 g, 1.19 mmol) and potassium carbonate (0.663 g, 4.80 mmol) in acetonitrile (15 mL) and DMF (5 mL) was added benzyl bromoacetate (0.21 mL, 1.33 mmol) under argon and the reaction was stirred at RT for 19 hr. The reaction was diluted with ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude product was carried forward without purification. ESI-MS m/z 363 (MH)+.

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was carried forward without purification

Sources & evidence

ORD record
ord-02a7ce027ba54f5ea68a571f6ee393fb
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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