Potassium Carbonate → HCID 69216052, compound

HRID 1392192Notes

Reaction equation

HRID 1392192 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).

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-0bfe2815a8374bc082b3da8dc7f36e35
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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