Potassium Carbonate → HCID 69216052, compound

HRID 2182627Notes

Reaction equation

HRID 2182627 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:10][C:11]1[CH:36]=[CH:35][C:14]([CH2:15][C:16]23[CH2:23][CH2:22][CH2:21][N:20]2[C:19](=[O:24])[N:18]([C:25]2[CH:30]=[C:29]([Cl:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=2)[C:17]3=[O:34])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C:16]23[CH2:23][CH2:22][CH2:21][N:20]2[C:19](=[O:24])[N:18]([C:25]2[CH:30]=[C:29]([Cl:31])[C:28]([O:32][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:27]([Cl:33])[CH:26]=2)[C:17]3=[O:34])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 22479224HCID 22479224, compound

Product 1

HCID 69216052HCID 69216052, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-bromobutyrate (28 mg) was added to a mixture of the compound from Example 135 (55 mg) and K2CO3 (18 mg) in 2 mL anhydrous DMF and the resulting mixture was heated at 80° C. for 5 hours. The solution was partitioned between EtOAc/H2O. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC to yield the titled compound (61 mg). MS (m/z) 583 (MH+).

Workup

  1. customThe solution was partitioned between EtOAc/H2O
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-2b7afcbce73e4d15a26c0478839d1039
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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