1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67208776, Verbindung

HRID 70834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70834
CCN=C=NCCCN(C)C.ON1C2N=CC=CC=2N=N1.[CH2:22]([O:29][C:30](=[O:40])[CH2:31][C:32]1([C:37]([OH:39])=O)[CH2:36][CH2:35][CH2:34][CH2:33]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OC(C1(CC(O)=O)CCCC1)=O)C1C=CC=CC=1.Cl.[C:61]([O:65][C:66](=[O:83])[CH2:67][CH:68]([NH2:82])[CH2:69][C:70]1[CH:75]=[CH:74][C:73]([C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)=[CH:72][CH:71]=1)([CH3:64])([CH3:63])[CH3:62].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:22]([O:29][C:30](=[O:40])[CH2:31][C:32]1([C:37]([NH:82][CH:68]([CH2:69][C:70]2[CH:75]=[CH:74][C:73]([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)=[CH:72][CH:71]=2)[CH2:67][C:66]([O:65][C:61]([CH3:64])([CH3:62])[CH3:63])=[O:83])=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

9

Edukt 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 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 EDCI (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-d6b0d04892bb4100ad0bc12c309f774a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822534B2

Notizen zur Reaktion

Wird geladen…