Diisopropylethylamine → HCID 178490379, Verbindung

HRID 333429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333429
[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.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].C1([C:38]2([C:44]([OH:46])=[O:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)CCCCC1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=N[C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][C:65]1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C)C=O.O>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[CH:65]1([CH:40]2[CH2:39][CH:38]([C:44]([OH:46])=[O:45])[CH2:43][CH2:42][N:41]2[C:12](=[O:14])[CH:11]([NH:10][C:9]([NH:8][CH2:7][CH2:6][C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[O:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669876094-Cyclohexyl-piperidine-4-carboxylic acid trifluoroacetateHCID 178490381HCID 178490381, Verbindung

Produkt 1

HCID 178490379HCID 178490379, VerbindungAusbeute 19,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution containing 93 mg (0.28 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propanoic acid and 100 mg (0.31 mmol) of 4-cyclohexyl-piperidine-4-carboxylic acid trifluoroacetate in 0.8 mL of dimethylformamide are added 0.16 mL of diisopropylethylamine and 90 mg (0.28 mmol) of TBTU. The reaction medium is stirred at room temperature for 18 hours. The reaction is stopped by adding water, and the organic compounds are extracted with dichloromethane. The organic phase is dried and evaporated. The oil obtained is purified by preparative HPLC (conditions cf. page 38). 35 mg of cyclohexyl-1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylic acid trifluoroacetate are obtained in a yield of 19%.

Aufarbeitung

  1. extractionthe organic compounds are extracted with dichloromethane
  2. customThe organic phase is dried
  3. customevaporated
  4. customThe oil obtained
  5. customis purified by preparative HPLC (conditions cf. page 38)

Quellen und Nachweise

ORD-Eintrag
ord-a934281c0c5c491eb36ce7a802c85b1a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877968B2

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