HCID 70194114, compound → HCID 70193506, compound

HRID 1533500Notes

Reaction equation

HRID 1533500 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([CH2:11][N:12]([CH2:42][C:43]([OH:45])=[O:44])[CH:13]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=1)[CH2:14][N:15]([CH2:28][C:29]([OH:31])=[O:30])[CH2:16][CH:17]([CH3:27])[N:18]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][C:20]([OH:22])=[O:21])([OH:10])=[O:9].[H][H]>[Pd].O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([CH2:11][N:12]([CH2:42][C:43]([OH:45])=[O:44])[CH:13]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=1)[CH2:14][N:15]([CH2:28][C:29]([OH:31])=[O:30])[CH2:16][CH:17]([CH3:27])[N:18]([CH2:19][C:20]([OH:22])=[O:21])[CH2:23][C:24]([OH:26])=[O:25])([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 70194114HCID 70194114, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 70193506HCID 70193506, compoundYield 125.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a Parr flask was added 3.40 g (3.84 mmol) of N,N,N′,N″,N″-Pentakis(carboxymethyl)-2-[(4-nitrophenyl)methyl-]-6-methyldiethylenetriamine trifluoroacetic acid salt and 50 ml of water followed by the addition of 0.3 g of 5% palladium on carbon. The flask was pressurized to 30 psi hydrogen and vented twice. The vessel was then pressurized to 45 psi hydrogen and shaken. Once hydrogen uptake ceased, typically after 2 to 4 hours, the flask was vented and the mixture filtered through a pad of celite. The celite was washed with 20 ml of water. The filtrate was concentrated under reduced pressure to afford 3.02 g of product with a yield of 92.03%. The spectral data obtained for this product are consistent with those of a reference standard.

Workup

  1. filtrationthe mixture filtered through a pad of celite
  2. washThe celite was washed with 20 ml of water
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d1d64e5e24b94293952e4428e7d70861
Source dataset
uspto-grants-2001_03
Patent number
US06207858B1

Reaction notes

Loading…