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 62582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62582
[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

Komponenten

4

Edukt 1

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

Produkt 1

HCID 867026522-{[5-(4-Aminophenyl)-2-[bis(carboxymethyl)amino]pentyl] ({2-[bis(carboxymethyl)amino]ethyl})amino}acetic acidAusbeute 115,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5ab1ece0d7604449868ea32fa8a64e61
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446995B2

Notizen zur Reaktion

Wird geladen…