Benzyl acrylate → HCID 10040049, compound

HRID 1418837Notes

Reaction equation

HRID 1418837 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.[C:20]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:23])[CH:21]=[CH2:22]>CN(C=O)C>[NH:9]([CH2:22][CH2:21][C:20]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:10]

Participants

5

Reactant 3

HCID 75617Benzyl acrylateHCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 10040049HCID 10040049, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of glycine t-butyl ester hydrochloride (20.7 g, 123 mmol) in DMF (50 mL) was added DIEA (21.5 mL, 123 mmol) and benzyl acrylate (20 g, 123 mmol). The mixture was allowed to stir at room temperature for 4 hours. This solution was concentrated in vacuo and the residue partitioned between saturated aqueous NaHCO3 and ethyl acetate and separated. The organic layer was washed once with saturated aqueous NaHCO3 and twice with brine. The ethyl acetate layer was dried (MgSO4), filtered and concentrated in vacuo to give 30 g (83%) of a slightly amber oil.

Workup

  1. concentrationThis solution was concentrated in vacuo
  2. customthe residue partitioned between saturated aqueous NaHCO3 and ethyl acetate
  3. customseparated
  4. washThe organic layer was washed once with saturated aqueous NaHCO3 and twice with brine
  5. dry with materialThe ethyl acetate layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give 30 g (83%) of a slightly amber oil

Sources & evidence

ORD record
ord-c24f5a06853f41e69df8e52a33cf854d
Source dataset
uspto-grants-1999_03
Patent number
US05885967

Reaction notes

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