Ethanol → (5-tert-Butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenoxy)-acetic acid ethyl ester

HRID 356548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356548
[OH:1][C:2]1[CH2:7][C:6]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[O:5][C:4](=[O:26])[CH:3]=1.[C:27]([C:31]1[C:32]([S:43]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:33][C:34]([CH3:42])=[C:35]([CH:41]=1)[O:36][CH2:37][C:38]([OH:40])=[O:39])([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH3:65][CH2:66]O>>[CH2:65]([O:40][C:38](=[O:39])[CH2:37][O:36][C:35]1[CH:41]=[C:31]([C:27]([CH3:28])([CH3:29])[CH3:30])[C:32]([S:43][C:3]2[C:4](=[O:26])[O:5][C:6]([CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)([CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)[CH2:7][C:2]=2[OH:1])=[CH:33][C:34]=1[CH3:42])[CH3:66]

Komponenten

6

Edukt 5

HCID 702EthanolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18798672[5-tert-Butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acidHCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Produkt 1

HCID 70253780(5-tert-Butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenoxy)-acetic acid ethyl ester

Versuchsvorschrift

The title compound was synthesized via General Method 9 using 209 mg (0.6 mmol) of 4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP), 250 mg (0.6 mmol) of [5-tert-butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acid (prepared in Example NNNN), 327 mg (2.4 mmol) of K2CO3, and DMF (2 mL). The reaction was conducted in EtOH to effect ester exchange. The reaction was worked up as described. The residue was chromatographed on silica gel eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH) to yield the product, m.p. 162°-163° C. 1H NMR (DMSO-d6) δ 1.21 (t, 3 H), 1.47 (s, 9 H), 1.8 (s, 3 H), 2.0 (m, 4 H), 2.6 (m, 6 H), 2.95 (s, 2 H), 4.25 (q, 2 H), 4.75 (s, 2 H), 6.65 (m, 5 H), 6.75 (s, 1 H), 7.0 (d 4 H), 9.18 (s, 2 H).

Aufarbeitung

  1. customThe residue was chromatographed on silica gel eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH)
  2. customto yield the product, m.p. 162°-163° C

Quellen und Nachweise

ORD-Eintrag
ord-1001d449b03b456b9ecd6bbf03c73de2
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834506

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