Acetic Acid → 1-(4-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzyl)azetidine-3-carboxylic acid

HRID 1710336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710336
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[C:12]2=[O:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[NH:29]1[CH2:32][CH:31]([C:33]([OH:35])=[O:34])[CH2:30]1.C([BH3-])#N.[Na+]>ClCCl.CO.CS(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:20][N:29]4[CH2:32][CH:31]([C:33]([OH:35])=[O:34])[CH2:30]4)=[CH:22][CH:23]=3)[C:12]2=[O:24])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 931923-azetidinecarboxylic AcidHCID 5003444Sodium cyanoborohydrideHCID 594568184-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzaldehyde

Produkt 1

HCID 247719691-(4-(3-(4-tert-Butylphenyl)-2-oxoimidazolidin-1-yl)benzyl)azetidine-3-carboxylic acidAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzaldehyde (32 mg, 0.1 mmol), acetic acid (50 μl) and azetidine-3-carboxylic acid (13 mg, 0.13 mmol) in dichloromethane/MeOH (1:1, 5 mL) was stirred at room temperature for 1 hour. Sodium cyanoborohydride (3.5 mg, 0.05 mmol) was added and the reaction mixture was stirred for 6 hour at room temperature. After concentration of solvent under reduced pressure, the resulting residue was dissolved in dimethylsulfoxide, filtered and purified by reverse phase preparative HPLC (Phenomenex reverse phase Luna 5u C18(2) column, 60×21.2 mm ID, mobile phase: A=0.05% TFA in water; B=0.05% TFA in acetonitrile. The flow rate was 10-12 mL/min) to yield the title product 4 mg (10%): 1H NMR (400 MHz, CDOD3) δ 7.72 (d, 2H), 7.51-7.40 (m, 6H), 4.33 (s, 2H), 4.28 (m, 4H), 4.02 (s, 4H), 3.64 (m, 1H), 1.32 (s, 9H). MS (ESI) m/z: Calculated: 407.22; Observed: 408.00 (M++1).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 6 hour at room temperature
  2. filtrationfiltered
  3. custompurified by reverse phase preparative HPLC (Phenomenex

Quellen und Nachweise

ORD-Eintrag
ord-a26a6cb982be419891de9650f07f65f0
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790707B2

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