Water → HCID 6950526, compound

HRID 1511863Notes

Reaction equation

HRID 1511863 reaction equation
[C:1](#N)[CH3:2].C(OC(ON1C(=O)CCC1=O)=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:22](=O)([O-])[O-:23].[K+].[K+].[OH2:28]>>[O:23]([CH2:22][C@@H:1]([OH:28])[CH3:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 83172Benzyl succinimido carbonate

Product 1

HCID 6950526HCID 6950526, compound

Procedure

To the appropriately substituted amine in a suitable organic solvent (preferably acetonitrile) and water mixture (about 1:1 to 8:1 ratio, preferably 4:1 ratio) is added N-(Benzyloxycarbonyloxy)succinimide (preferably 1 equivalent) followed by potassium carbonate (preferably 1 equivalent). The reaction mixture is stirred at ambient temperature for a period of 1-4 hours (preferably 1 hour). The solvent is then removed and the remaining aqueous slurry is taken up in water and organic solvent (preferably ethyl acetate). The organic layer is washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting crude can be purified by column chromatography to give the desired product.

Workup

  1. customThe solvent is then removed
  2. washThe organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude can be purified by column chromatography

Sources & evidence

ORD record
ord-d7a85cf819284dcfa219af3777d67cfa
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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