Potassium Carbonate → HCID 71697075, compound

HRID 517577Notes

Reaction equation

HRID 517577 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[NH:17][C:18](=[O:20])[CH2:19]/2)=[CH:12][CH:11]=1)[CH3:8].Br[CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C>CN(C=O)C>[NH2:27][CH2:26][CH2:25][N:17]1[C:18](=[O:20])[CH2:19]/[C:15](=[CH:14]\[C:13]2[CH:22]=[CH:23][C:10]([O:9][CH2:7][CH3:8])=[CH:11][CH:12]=2)/[C:16]1=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 64435232HCID 64435232, compound

Product 1

HCID 71697075HCID 71697075, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (180 mg, 1.30 mmol) was added to a solution of compound 12 (100 mg, 0.43 mmol) in 3 mL of anhydrous DMF at 0° C. After stirring the reaction mixture for 20 min, a solution of tert-butyl (2-bromoethyl)carbamate (96 mg, 0.43 mmol) in anhydrous DMF (1 mL) was added and then the reaction mixture was stirred at room temperature for 3 h. The reaction was quenched by adding water and extracted with ethyl acetate. The ethyl acetate layer was washed with 10% NH4Cl aqueous solution followed by water and dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (20% ethyl acetate in hexanes) to afford 70 mg (43.2%) of Boc-protected 13 as a white solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 3 h
  2. customThe reaction was quenched
  3. additionby adding water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with 10% NH4Cl aqueous solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica column chromatography (20% ethyl acetate in hexanes)
  10. customto afford 70 mg (43.2%) of Boc-

Sources & evidence

ORD record
ord-3df0350b7285426fa27fa836f5de4959
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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