4-Acetylmorpholine → 2-(4-morpholinyl)-8-phenoxy-4H-1-benzopyran-4-one

HRID 750457

Reaktionsgleichung

[C:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[O:10]([C:17]1[C:18](O)=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20](OC)=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>>[N:4]1([C:1]2[O:3][C:18]3[C:17]([O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:26][CH:25]=[CH:24][C:19]=3[C:20](=[O:21])[CH:2]=2)[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Komponenten

Edukt 3

HCID 155434-Acetylmorpholine

HCID 67749Trifluoromethanesulfonic anhydride

HCID 22263553Methyl 3-phenoxy-2-hydroxybenzoate

Produkt 1

HCID 98802482-(4-morpholinyl)-8-phenoxy-4H-1-benzopyran-4-oneAusbeute 27,8 %

Versuchsvorschrift

Condensation of the lithium enolate of N-acetyl morpholine (0.21 g, 1.6 mmol) with methyl 3-phenoxy-2-hydroxybenzoate (0.25 g, 1.0 mmol) followed by cyclodehydration with trifluoromethanesulfonic anhydride (0.60 ml, 3.6 mmol) as described above yielded TGX-134 as an off-white solid (0.090 g).

Quellen und Nachweise

ORD-Eintrag: ord-8c03aa44a2974e7888ebca03c4e0997d
Quelldatensatz: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07405211B2

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