Potassium Carbonate → HCID 86722963, compound

HRID 1486172Notes

Reaction equation

HRID 1486172 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-97c2691441494042a164f685f5b4a34a
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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