Diisopropylethylamine → HCID 178490380, Verbindung

HRID 333414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333414
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[N:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:56]1([C:62]([CH:64]2[CH2:67][NH:66][CH2:65]2)=[O:63])[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1>ClCCl.CN(C)C=O>[CH:56]1([C:62]([CH:64]2[CH2:67][N:66]([C:12](=[O:14])[CH:11]([NH:10][C:9]([NH:8][CH2:7][CH2:6][C:4]3[N:3]=[CH:2][NH:1][CH:5]=3)=[O:24])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:65]2)=[O:63])[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669879923-CyclohexanecarbonylazetidineHCID 178490381HCID 178490381, Verbindung

Produkt 1

HCID 178490380HCID 178490380, VerbindungAusbeute 3,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 189 mg (0.57 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxy-phenyl)propanoic acid (cf. preparation 2-3) dissolved in 3.5 mL of dichloromethane and 1.0 mL of dimethylformamide are added 0.2 mL (1.14 mmol) of diisopropylethylamine, 202 mg (0.63 mmol) of TBTU and 95 mg (0.57 mmol) of 3-cyclohexanecarbonylazetidine. After 5 hours, the solution is washed with 1N sodium hydroxide solution and the organic products are extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product obtained is purified by preparative TLC (9/1 dichloromethane/methanol). 8.5 mg of 1-[2-(3-cyclohexanecarbonylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-3-[2-(1H-imidazol-4-yl)ethyl]urea are obtained in a yield of 3%.

Aufarbeitung

  1. washthe solution is washed with 1N sodium hydroxide solution
  2. extractionthe organic products are extracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customis purified by preparative TLC (9/1 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-04729aef328349a8b7a518d9aaf7670d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877968B2

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