Diisopropylethylamine → HCID 178491635, Verbindung

HRID 710296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710296
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].O[NH:14][C:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)=[NH:16].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][NH:16][C:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)=[NH:14])=[O:6]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 1699823-Chloro-p-anisic acidHCID 2733179PyBroPHCID 178513238HCID 178513238, Verbindung

Produkt 1

HCID 178491635HCID 178491635, VerbindungAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the product of Step B (0.25 g; 1.43 mmol), and the product of Step C (0.23 g; 1.31 mmol) in anhydrous THF (5 ml), PyBroP (0.67 g; 1.44 mmol) was added followed by DIPEA (0.57 ml; 3.3 mmol), with stirring, at room temperature under N2. After 1 h of stirring, the mixture was diluted to 20 ml with EtOAc, washed with saturated NH4Cl (5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by crystallization from EtOAc/hexane to give the title compound (0.42 g; 93%), as a creamy solid. 1H-NMR (CD3OD) 3.96 (s, 3H); 5.41 (s, 1H); 6.52 (d, 1H, J=3.2 Hz); 7.14 (d, 1H, J=8.7 Hz); 7.27 (d, 1H, J=3.2 Hz); 7.41-7.77 (m, 2H); 8.0 (s, 1H); 8.11 (dd, 1H, J=2; 8.7 Hz); 8.15 (d, 1H, J=2 Hz).

Aufarbeitung

  1. stirringAfter 1 h of stirring
  2. washwashed with saturated NH4Cl (5 ml), brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe residue was purified by crystallization from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d9dd7e0ed20a4de39a718bcf6393fba2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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