Sodium Iodide → Benzyl glycinate

HRID 1757782Notes

Reaction equation

HRID 1757782 reaction equation
[NH2:1][C:2]1C=C(C(NCCCCCCCCCC)=O)C=C(C(NCCCCCCCCCC)=O)C=1.[CH2:34](C(Br)C([O-])=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[I-].[Na+].[C:48](=[O:51])([O-])[O-:49].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:35]1([CH2:34][O:49][C:48](=[O:51])[CH2:2][NH2:1])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 193889485-amino-N,N'-didecyl-1,3-benzenedicarboxamideHCID 21881508Benzylbromoacetate

Product 1

HCID 409140Benzyl glycinate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.0 g (15.2 mmol) of 5-amino-N,N'-didecyl-1,3-benzenedicarboxamide, 9.7 ml of benzylbromoacetate, 4.6 g (30.4 mmol) of sodium iodide and 4.2 g (30.4 mmol) of potassium carbonate in 150 ml of acetone and 50 ml of DMF was stirred at reflux for 26 hours. The reaction mixture was filtered and the solvents were removed from the filtrate at reduced pressure. The residue was purified by HPLC using 35% ethyl acetate-hexane. The pure fractions were combined and recrystallized from methylene chloride-ether to give 4.3g (47% yield, mp 102°-104°) of N-[3,5-bis[decylamino)carbonyl]phenyl]glycine phenylmethyl ester. The nmr spectrum was consistent with the structure.

Workup

  1. temperatureat reflux for 26 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe solvents were removed from the filtrate at reduced pressure
  4. customThe residue was purified by HPLC
  5. customrecrystallized from methylene chloride-ether

Sources & evidence

ORD record
ord-b6e5fb40cf1449fc916d8ed1c959077c
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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