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Diisopropylethylamine → HCID 58136363, Verbindung

HRID 877184
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 877184
[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7](O)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH:34]([CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH2:33]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C>[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7]([NH:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH:34]([CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH2:33]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

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 66893992HCID 66893992, Verbindung

Produkt 1

HCID 58136363
HCID 58136363, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 590 mg (1.5 mmol) of cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid (enantiomer 2; Example 77A), 400 mg (1.8 mmol) of methyl 3-(3-aminocyclohexyl)propanoate hydrochloride (mixture of isomers), 1.05 ml (6.0 mmol) of N,N-diisopropylethylamine and 857 mg (2.26 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) in 13 ml of DMF was stirred at room temperature overnight. After the reaction had ended, the reaction mixture was poured onto ice-water, whereupon the target compound precipitated in the form of white crystals. After filtration, the crystals obtained were washed three times with water and then dried overnight at 40° C. in a vacuum drying cabinet. This gave 830 mg (1.58 mol, 98% of theory) of the title compound as a mixture of diastereomers.

Aufarbeitung

  1. additionthe reaction mixture was poured onto ice-water, whereupon the target compound
  2. customprecipitated in the form of white crystals
  3. filtrationAfter filtration
  4. customthe crystals obtained
  5. washwere washed three times with water
  6. customdried overnight at 40° C. in a vacuum
  7. customdrying cabinet
  8. additionThis gave 830 mg (1.58 mol, 98% of theory) of the title compound as a mixture of diastereomers

Quellen und Nachweise

ORD-Eintrag
ord-bd5c5d04f44b42b7ac29d94945daeb76
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987256B2

Notizen zur Reaktion

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