Reaktionsgleichung
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:12])[CH2:11][CH2:10][S:9][CH2:8][CH2:7]1)=[O:5].[OH:13][C:14]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:2][O:3][C:4]([C:6]1([NH:12][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[C:22]([CH3:23])[C:14]=2[OH:13])[CH2:7][CH2:8][S:9][CH2:10][CH2:11]1)=[O:5]Komponenten
7
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of HCl salt of 4-amino-tetrahydro-thiopyran-4-carboxylic acid methyl ester (529 mg, 2.5 mmol), 2-hydroxy-3-methyl-benzoic acid (380 mg, 2.5 mmol), HATU (1.14 g, 3.0 mmol) in anhydrous DMF (20 mL) is added DIPEA (1.66 mL, 10 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (30 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 10-80% EtOAc in heptane) to give a pure product (27) as white solid (102 mg, 13%).
Aufarbeitung
- customAfter the removal of DMF in vacuo
- dissolutionthe residue is dissolved in EtOAc (30 mL)
- washwashed with water (1×10 mL) and brine (2×10 mL)
- dry with materialThe organic layer is dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue is purified by flash column chromatography (115 g silica gel, gradient elution: 10-80% EtOAc in heptane)
Quellen und Nachweise
- ORD-Eintrag
- ord-fb5b094bc0f940f4bcca61c454ca535d
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08569535B2
Verknüpfte Notizen
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