Sodium Hydroxide → N-[(R)-6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-hydroxy-acetamide
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C@H:17]([CH2:21][NH:22][C:23]([CH2:25][O:26]C(=O)C)=[O:24])[CH2:16][CH2:15][CH2:14]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C@H:17]([CH2:21][NH:22][C:23](=[O:24])[CH2:25][OH:26])[CH2:16][CH2:15][CH2:14]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
Acetic acid {[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-methyl ester (0.1 g) was dissolved in 10 mL methanol, and 2 mL of 2M aqueous NaOH was added. The reaction mixture was heated to 60° C. with stirring for 20 minutes, then cooled and concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate, and the organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. The oily residue was recrystallized from methyl tert-butyl ether/hexanes (1:1) to 80 mg of N—[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-hydroxy-acetamide, MS (M+H)=378.
Aufarbeitung
- temperaturecooled
- concentrationconcentrated under reduced pressure
- customThe residue was partitioned between water and ethyl acetate
- customthe organic layer was separated
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe oily residue was recrystallized from methyl tert-butyl ether/hexanes (1:1) to 80 mg of N—[(R)-6-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-2-hydroxy-acetamide, MS (M+H)=378
Quellen und Nachweise
- ORD-Eintrag
- ord-7304277a7ae84ec2a17109bbcf430c28
- Quelldatensatz
- uspto-grants-2011_07
- Patentnummer
- US07981923B2
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