Vinyl Acetate → HCID 89422245, compound

HRID 1527652Notes

Reaction equation

HRID 1527652 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](OC=C)(=O)[CH3:18].[OH-].[K+]>[Pd].C(OCC)C>[CH:17]([O:15][C:14](=[O:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH2:18]

Participants

6

Reactant 3

HCID 7904Vinyl AcetateHCID 14797Potassium HydroxideHCID 23591750t-Boc-N-amido-PEG1-acid

Product 1

HCID 89422245HCID 89422245, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

3-(2-tert-Butoxycarbonylamino-ethoxy)-propionic acid (3.72 g, 15.95 mmol) was dissolved in vinyl acetate (147 mL, 1595 mmol). Pd (II) acetate (716 mg, 3.19 mmol) and KOH (89 mg, 1.59 mmol) were added to the reaction mixture and stirred overnight. The reaction mixture was transferred into a large excess of diethyl ether to fully precipitate the black Pd byproduct. The solution plus precipitate was then filtered through celite to remove the black precipitate. The resulting solution was then concentrated to dryness and the product purified on a silica column using ethyl acetate/hexane eluent. Yield=60%.

Workup

  1. customto fully precipitate the black Pd byproduct
  2. filtrationThe solution plus precipitate was then filtered through celite
  3. customto remove the black precipitate
  4. concentrationThe resulting solution was then concentrated to dryness
  5. customthe product purified on a silica column

Sources & evidence

ORD record
ord-83a962b639f6460e824b98f2ecb80721
Source dataset
uspto-grants-2015_07
Patent number
US09089611B2

Reaction notes

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