Potassium Carbonate → HCID 68900004, compound

HRID 1828971Notes

Reaction equation

HRID 1828971 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH:10]([CH3:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([OH:19])[CH:13]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH:29](Br)[C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C>[CH2:33]([O:32][C:30]([CH:29]1[O:18][C:15]2[CH:16]=[CH:17][C:12]([CH2:11][CH:10]([N:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:21])[CH2:8][CH3:9])[CH3:20])=[CH:13][C:14]=2[O:19]1)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69237Ethyl dibromoacetateHCID 70986816[2-(3,4-Dihydroxy-phenyl)-1-methyl-ethyl]-ethyl-carbamic acid tert-butyl ester

Product 1

HCID 68900004HCID 68900004, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To 2 g (6.7 mmol) of 2C was added 40 mL of anhydrous DMF followed by 3.5 g (25 mmol) of anhydrous K2CO3, 5 g of 3 A° molecular sieves and 3.2 mL (25 mmol) of ethyl dibromoacetate. The reaction mixture was heated at 120° C. for 3 hours under argon atmosphere and then concentrated under reduced pressure. To the residue 75 mL of ethyl acetate were added and filtered. To the filtrate 75 mL of water were added and transferred to a separatory funnel. The organic layer was separated, and the aqueous layer was extracted with 5×75 mL of ethyl acetate. All the organic layers were combined, dried (anhydrous Na2SO4), and concentrated to dryness. The residue was purified by silica gel column chromatography using 10% ethyl acetate in hexane to give 954 mg (5.3 mmol, 37%) of 2D as a colorless gum (M+Na, 402).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue 75 mL of ethyl acetate were added
  3. filtrationfiltered
  4. additionTo the filtrate 75 mL of water were added
  5. customtransferred to a separatory funnel
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with 5×75 mL of ethyl acetate
  8. dry with materialdried (anhydrous Na2SO4)
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7a08d05f0a52457d8c83236575f3f28e
Source dataset
uspto-grants-2006_06
Patent number
US07060847B2

Reaction notes

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