HCID 19388922, compound → HCID 19389040, compound

HRID 1757833Notes

Reaction equation

HRID 1757833 reaction equation
[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([N+:35]([O-])=O)[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2]>[Pd].C1COCC1.CN(C=O)C>[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([NH2:35])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2]

Participants

5

Reactant 1

HCID 19388922HCID 19388922, compound

Product 1

HCID 19389040HCID 19389040, compoundYield 44.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.6 g of N-(carboxymethyl)-N-[3-nitro-5-(octadecyloxy)phenyl]glycine and 0.2 g of 10% palladium on carbon in 170 ml of THF and 10 ml of DMF was stirred in ahydrogen atmosphere at room temperature until uptake ceased after 4 hours. The reaction mixture was heated to dissolve the precipitated product and the catalyst was removed by filtration. The filtrate was concentrated at reduced pressure and the solid residue was dissolved in THF and the solution was passed through a SEP-PAK silica cartridge (Waters Associates). The eluent was concentrated at reduced pressure to a solid which was triturated with ethyl acetate and filtered to give 0.25 g (44% yield, mp 185°-195°) of N-(carboxymethyl)-N-[3-amino-5-(octadecyloxy)phenyl]glycine. The structurewas confirmed by nmr and mass spectra.

Workup

  1. temperatureThe reaction mixture was heated
  2. dissolutionto dissolve the precipitated product
  3. customthe catalyst was removed by filtration
  4. concentrationThe filtrate was concentrated at reduced pressure
  5. dissolutionthe solid residue was dissolved in THF
  6. concentrationThe eluent was concentrated at reduced pressure to a solid which
  7. customwas triturated with ethyl acetate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-888c88dcd0ac47d1b4674cac38d049fa
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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