Tetrahydrofuran → (1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid

HRID 422173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 422173
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([C:21]([O-:23])=[O:22])[CH:18]=[C:17]2[C:4]=1[C@H:5]1[C@H:14]([CH2:15][S:16]2(=[O:25])=[O:24])[C@:13]2([CH3:26])[C@H:8]([C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1.O[Li].O.[CH2:32]1COCC1>O>[CH3:1][O:2][C:3]1[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[C:17]2[C:4]=1[C@@:5]1([CH3:32])[C@H:14]([CH2:15][S:16]2(=[O:25])=[O:24])[C@:13]2([CH3:26])[C@H:8]([C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86654190(1R,10S,11S,16S)-3-methoxy-11,15,15-trimethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylate

Produkt 1

HCID 53240648(1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of (1R,10S,11S,16S)-3-methoxy-11,15,15-trimethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylate (59) (0.29 g, 0.66 mmol) and LiOH.H2O (0.08 g, 3.3 mmol) in THF (15 mL) and water (5.0 mL) was stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure and the residue was acidified with 1 M HCl. The resulting solid was collected by filtration to give (1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid (80) (0.27 g, 98%) as a white solid. 1H NMR (CD3OD): δ 8.04 (d, 1H), 7.74 (d, 1H), 3.94 (s, 3H), 3.47-3.35 (m, 3H), 2.26 (d, 1H), 1.86-1.16 (m, 11H), 1.10-1.00 (m, 5H), 0.89 (s, 3H), 0.87 (s, 3H). MS m/z 421 (O23H32O5S+H+).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. filtrationThe resulting solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-8f4f1754d415413ab5f6fb60ef090896
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101605B2

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