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Diisopropylethylamine → HCID 58074493, Verbindung

HRID 238187
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 238187
CCN(C(C)C)C(C)C.[CH:10]1([CH:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][N:26]3[C:31](=[O:32])[CH2:30][O:29][C:28]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[N:27]3)=[CH:21][CH:20]=2)[C:16](O)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1.[NH2:39][CH:40]([CH3:54])[CH2:41][CH2:42][CH2:43][C:44]1([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:46][CH2:45]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH:10]1([CH:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][N:26]3[C:31](=[O:32])[CH2:30][O:29][C:28]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[N:27]3)=[CH:21][CH:20]=2)[C:16]([NH:39][CH:40]([CH3:54])[CH2:41][CH2:42][CH2:43][C:44]2([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:45][CH2:46]2)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58074507cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acidHCID 58074508HCID 58074508, Verbindung

Produkt 1

HCID 58074493
HCID 58074493, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

At RT, 253 μl (1.45 mmol) of DIEA were added to a solution of 517.9 mg (1.32 mmol) of (+)-cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid and 450 mg (about 1.98 mmol, crude material) of tert-butyl 1-(4-aminopentyl)cyclo-propanecarboxylate in 2.5 ml of DMF. The resulting mixture was cooled to 0° C., and four portions of altogether 186.4 mg (0.49 mmol) of HATU were then added. The reaction mixture was slowly warmed to RT, stirred at RT for 16 h and then added to water and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. Purification of the crude product by preparative RP-HPLC (acetonitrile/water gradient) gave 540.0 mg (68.0% of theory) of the target compound as a diastereomer mixture.

Aufarbeitung

  1. temperatureThe reaction mixture was slowly warmed to RT
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the crude product by preparative RP-HPLC (acetonitrile/water gradient)
  6. customgave 540.0 mg (68.0% of theory) of the target compound as a diastereomer mixture

Quellen und Nachweise

ORD-Eintrag
ord-39a84fc6bc4444a7b474cca3a20590a5
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642592B2

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