2-({2-[Bis(carboxymethyl)amino]-5-(4-nitrophenyl)pentyl}({2-[bis(carboxymethyl)amino]ethyl})amino)acetic acid → 2-{[5-(4-Aminophenyl)-2-[bis(carboxymethyl)amino]pentyl] ({2-[bis(carboxymethyl)amino]ethyl})amino}acetic acid

HRID 62582Notes

Reaction equation

HRID 62582 reaction equation
[C:1]([CH2:4][N:5]([CH2:36][C:37]([OH:39])=[O:38])[CH:6]([CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=1)[CH2:7][N:8]([CH2:13][CH2:14][N:15]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][C:17]([OH:19])=[O:18])[CH2:9][C:10]([OH:12])=[O:11])([OH:3])=[O:2]>C(O)C.[Pd]>[NH2:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][CH2:25][CH2:24][CH:6]([N:5]([CH2:36][C:37]([OH:39])=[O:38])[CH2:4][C:1]([OH:3])=[O:2])[CH2:7][N:8]([CH2:13][CH2:14][N:15]([CH2:16][C:17]([OH:19])=[O:18])[CH2:20][C:21]([OH:23])=[O:22])[CH2:9][C:10]([OH:12])=[O:11])=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 867026502-({2-[Bis(carboxymethyl)amino]-5-(4-nitrophenyl)pentyl}({2-[bis(carboxymethyl)amino]ethyl})amino)acetic acid

Product 1

HCID 867026522-{[5-(4-Aminophenyl)-2-[bis(carboxymethyl)amino]pentyl] ({2-[bis(carboxymethyl)amino]ethyl})amino}acetic acidYield 115.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5b (36 mg, 0.0541 mmol) in ethanol (9 mL) at room temperature was added 10% Pd/C (10 mg) under Ar (g). The reaction mixture was placed under hydrogenation apparatus for 24 h. The resulting mixture was filtered via celite bed and washed thoroughly with methanol. The filtrate was concentrated to provide 6b (33 mg, 91%) as a yellowish solid. 1H NMR (D2O, 300 MHz) δ1.03-2.15 (m, 5H), 2.20-4.40 (m, 18H), 7.38 (s, 4H).

Workup

  1. filtrationThe resulting mixture was filtered via celite bed
  2. washwashed thoroughly with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5ab1ece0d7604449868ea32fa8a64e61
Source dataset
uspto-grants-2016_09
Patent number
US09446995B2

Reaction notes

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