Diisopropylethylamine → HCID 67208776, Verbindung

HRID 1945011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945011
CCN=C=NCCCN(C)C.Cl.ON1C2N=CC=CC=2N=N1.[CH2:23]([O:30][C:31](=[O:41])[CH2:32][C:33]1([C:38]([OH:40])=O)[CH2:37][CH2:36][CH2:35][CH2:34]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OC(C1(CC(O)=O)CCCC1)=O)C1C=CC=CC=1.Cl.[C:62]([O:66][C:67](=[O:84])[CH2:68][CH:69]([NH2:83])[CH2:70][C:71]1[CH:76]=[CH:75][C:74]([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)=[CH:73][CH:72]=1)([CH3:65])([CH3:64])[CH3:63].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:23]([O:30][C:31](=[O:41])[CH2:32][C:33]1([C:38]([NH:83][CH:69]([CH2:70][C:71]2[CH:76]=[CH:75][C:74]([C:77]3[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=3)=[CH:73][CH:72]=2)[CH2:68][C:67]([O:66][C:62]([CH3:65])([CH3:63])[CH3:64])=[O:84])=[O:40])[CH2:34][CH2:35][CH2:36][CH2:37]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

9

Edukt 6

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 216902921-Carboxymethyl-cyclopentanecarboxylic acid benzyl esterHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 67208761HCID 67208761, Verbindung

Produkt 1

HCID 67208776HCID 67208776, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Next, to a solution of EDCl (51.2 mg, 0.267 mmol), 1-hydroxy-7-azabenzotriazole (36.4 mg, 0.267 mmol) and 6:1 mixture of 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid and 2-(1-(benzyloxycarbonyl)cyclopentyl)acetic acid (65.6 mg, 0.214 mmol) in DMF (1 ml), which is stirred for 1.5 hours in advance, the crude 3-amino-4-biphenyl-4-yl-butyric acid tert-butyl ester hydrochloride and DIPEA (0.093 ml, 0.535 mmol) are added. After stirring for 2.5 hours, the reaction mixture is diluted with H2O, and the products are extracted with EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated. The obtained residue is purified by silica gel flash column chromatography (heptane/EtOAc=100:0 to 0:100) to give crude tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-4-(biphenyl-4-yl)butanoate (38 mg).

Aufarbeitung

  1. stirringAfter stirring for 2.5 hours
  2. extractionthe products are extracted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe obtained residue is purified by silica gel flash column chromatography (heptane/EtOAc=100:0 to 0:100)

Quellen und Nachweise

ORD-Eintrag
ord-a019182c99034d2ca6b81e0bcca01d25
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394853B2

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