Sodium Iodide → Benzyl glycinate

HRID 1110301Notes

Reaction equation

HRID 1110301 reaction equation
O=C(OC1C=C([NH2:31])C=CC=1OC(=O)CCCCCCCCC)CCCCCCCCC.Br[CH2:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:38]1([CH2:37][O:36][C:34](=[O:35])[CH2:33][NH2:31])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 19389092HCID 19389092, compound

Product 1

HCID 409140Benzyl glycinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.5 g (5.77 mmol) of 3,4-bis[(1-oxodecyl)oxy]benzenamine, 9.1 ml (57.7 mmol) of benzyl bromoacetate, 3.1 g (14.4 mmol) of 1,8-bis(dimethylamino)naphthalene and 0.34 g (2.3 mmol) of sodium iodide in 50 ml of acetonitrile and 10 ml of DMF was stirred at reflux for 48 hours. The solvents were removed at reduced pressure and the residue was treated with methylene chloride and water. The organic phase was separated, dried and concentrated to an oil which was purified by HPLC using 20% ethyl acetate-hexane to give 2.2 g (52% yield) of N-[3,4-bis[(1-oxodecyl)oxy]phenyl]-N-[2-oxo-2-phenylmethoxy)ethyl]glycine phenylmethyl ester as an oil. The structure was confirmed by nmr and mass spectra.

Workup

  1. temperatureat reflux for 48 hours
  2. customThe solvents were removed at reduced pressure
  3. additionthe residue was treated with methylene chloride and water
  4. customThe organic phase was separated
  5. customdried
  6. concentrationconcentrated to an oil which
  7. customwas purified by HPLC

Sources & evidence

ORD record
ord-0d9ae554b4e041199158b4649ad88785
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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