Lithium borohydride → Methyl 2-[4-([4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl]oxymethyl)phenoxy]-6-methoxybenzoate

HRID 724702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724702
[BH4-].[Li+].[O:3]=[S:4]1(=[O:38])[C:8]([C:9]2[CH:36]=[CH:35][C:12]([CH2:13][O:14][CH2:15][C:16]3[CH:34]=[CH:33][C:19]([O:20][C:21]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[C:22]=4[C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[CH:7][C:6](=[O:37])[NH:5]1>O1CCCC1>[O:3]=[S:4]1(=[O:38])[CH:8]([C:9]2[CH:36]=[CH:35][C:12]([CH2:13][O:14][CH2:15][C:16]3[CH:34]=[CH:33][C:19]([O:20][C:21]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[C:22]=4[C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)[CH2:7][C:6](=[O:37])[NH:5]1

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 58746605Methyl 2-[4-([4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]oxymethyl)phenoxy]-6-methoxybenzoate

Produkt 1

HCID 58746691Methyl 2-[4-([4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl]oxymethyl)phenoxy]-6-methoxybenzoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2 M Lithium borohydride in tetrahydrofuran (0.045 mL, 0.090 mmol) was added to methyl 2-[4-([4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]oxymethyl)phenoxy]-6-methoxybenzoate (8 mg, 0.02 mmol) in tetrahydrofuran (1 mL). After stirring at ambient temperature for one hour, the reaction was quenched with saturated aqueous ammonium chloride. The product was purified on a 50 mm Luna C18 column using a 20–100% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 30 mL per minute over a 30 minute period. The major product was lyophilized to give a white powder (7 mg, 87%). 1H NMR (400 MHz, CDCl3): δ 7.47 (d, J=7.1 Hz, 2H), 7.42 (d, J=7.1 Hz, 2H), 7.31 (m, 4H), 6.68 (d, J=8.6 Hz, 1H), 6.48 (d, J=8.6 Hz, 1H), 4.98 (t, J=8.4 Hz, 1H), 4.56 (m, 4H), 3.87 (s, 3H), 3.85 (s, 3H), 3.37 (m, 2H); LCMS found for C26H25NNaO8S (M+Na)+: m/z=534.0.

Aufarbeitung

  1. customthe reaction was quenched with saturated aqueous ammonium chloride
  2. customThe product was purified on a 50 mm Luna C18 column
  3. customover a 30 minute

Quellen und Nachweise

ORD-Eintrag
ord-6066dc22b1374037956330c59a41e4a9
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141596B2

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