Potassium Carbonate → HCID 69489637, compound

HRID 1296755Notes

Reaction equation

HRID 1296755 reaction equation
[CH2:1]([NH:8][C:9]1[CH:29]=[C:28]([C:30]2[N:34]=[C:33]([CH3:35])[O:32][N:31]=2)[CH:27]=[CH:26][C:10]=1[CH2:11][NH:12][C:13](=[O:25])[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([CH3:22])=[C:16]([O:23][CH3:24])[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:37][C:38]([O:40]C)=[O:39].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:8]([CH2:37][C:38]([OH:40])=[O:39])[C:9]1[CH:29]=[C:28]([C:30]2[N:34]=[C:33]([CH3:35])[O:32][N:31]=2)[CH:27]=[CH:26][C:10]=1[CH2:11][NH:12][C:13](=[O:25])[C:14]1[CH:15]=[C:16]([O:23][CH3:24])[C:17]([CH3:22])=[C:18]([O:20][CH3:21])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 69491442HCID 69491442, compound

Product 1

HCID 69489637HCID 69489637, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 23a (163 mg, 0.35 mmol), methyl bromoacetate (0.166 mL, 1.75 mmol), and potassium carbonate (145 mg, 1.05 mmol) in DMF (2 mL) was sealed in a pressure tube and heated at 80° C. overnight. The reaction mixture was filtered through a silica gel pad in ethyl acetate and concentrated on a rotary evaporator. The residue was dissolved in a mixture of THF (3 mL) and MeOH (1 mL) and 10% LiOH (2 mL) was added. The reaction mixture was stirred overnight at rt. The reaction mixture was concentrated on a rotary evaporator, dissolved in water (50 mL), and acidified with conc. HCl. The white precipitate was filtered and dried invacuo to give compound 23b (155 mg, 83%). ESI-MS m/e 531.3 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a silica gel pad in ethyl acetate
  2. concentrationconcentrated on a rotary evaporator
  3. dissolutionThe residue was dissolved in a mixture of THF (3 mL) and MeOH (1 mL) and 10% LiOH (2 mL)
  4. additionwas added
  5. concentrationThe reaction mixture was concentrated on a rotary evaporator
  6. dissolutiondissolved in water (50 mL)
  7. filtrationThe white precipitate was filtered
  8. customdried invacuo

Sources & evidence

ORD record
ord-626869136adb4ce0abdb430767e81b0a
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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