Potassium Carbonate → 5-[2-(tert-butoxycarbonyl-ethyl-amino)-propyl]-benzo[1,3]dioxole-2-carboxylic Acid Ethyl Ester

HRID 2099711Notes

Reaction equation

HRID 2099711 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 689000045-[2-(tert-butoxycarbonyl-ethyl-amino)-propyl]-benzo[1,3]dioxole-2-carboxylic Acid Ethyl EsterYield 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-9ac28dae651141e19f7d2472479a6ddb
Source dataset
uspto-grants-2009_08
Patent number
US07569676B2

Reaction notes

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