2-({2-[Bis(carboxymethyl)amino]-3-(4-nitrophenyl)propyl}({2-[bis(carboxymethyl)amino]ethyl})amino)acetic acid → 2-[[3-(4-Aminophenyl)-2-[bis(carboxymethyl)amino]propyl]-[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid

HRID 62581Notes

Reaction equation

HRID 62581 reaction equation
[C:1]([CH2:4][N:5]([CH2:34][C:35]([OH:37])=[O:36])[CH:6]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=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]>O.[Pd]>[NH2:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH:6]([N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:34][C:35]([OH:37])=[O:36])[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:26][CH:27]=1

Participants

4

Reactant 1

HCID 103488702-({2-[Bis(carboxymethyl)amino]-3-(4-nitrophenyl)propyl}({2-[bis(carboxymethyl)amino]ethyl})amino)acetic acid

Product 1

HCID 1315962-[[3-(4-Aminophenyl)-2-[bis(carboxymethyl)amino]propyl]-[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acidYield 119.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of 5a (32 mg, 0.0502 mmol) in H2O (9 mL) at room temperature was added 10% Pd/C (13 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 H2O. The filtrate was concentrated to provide 6a (30 mg, 93%) as a yellowish solid. 1H NMR (D2O, 300 MHz) δ 2.43-4.25 (m, 22H), 7.21 (s, 4H).

Workup

  1. filtrationThe resulting mixture was filtered via celite bed
  2. washwashed thoroughly with H2O
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-61924f1d97a049a38e70581243f5d27b
Source dataset
uspto-grants-2016_09
Patent number
US09446995B2

Reaction notes

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