Hydrochloric Acid → Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-, methyl ester

HRID 1671742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1671742
[OH:1][C@H:2]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)/[CH:3]=[CH:4]/[C:5]#[C:6]/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C@H:11]1[O:15]C(C)(C)[O:13][C@H:12]1[CH2:18][O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].Cl>CO>[F:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:25][C@@H:2]([OH:1])/[CH:3]=[CH:4]/[C:5]#[C:6]/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C@@H:11]([OH:15])[C@@H:12]([OH:13])[CH2:18][O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 865940532-[[(4S,5R)-5-[(1E,3E,7E,9S)-9-hydroxy-10-(4-fluorophenoxy)-1,3,7-decatrien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester

Produkt 1

HCID 9823441Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-, methyl esterAusbeute 145,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 2-[[(4S,5R)-5-[(1E,3E,7E,9S)-9-hydroxy-1 0-(4-fluorophenoxy)-1,3,7-decatrien-5-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester, (1.1 g, 1.8 mmol) in methanol (25 mL) was treated with 1 mL of 1 N hydrochloric acid and the reaction was stirred for 2 days. The pH of the reaction was adjusted to neutrality. Purification on preparative reverse phase semi-prep column using a gradient of acetonitrile in water yielded 1.1 g of (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-1 1-ynoic acid, methyl ester, as an oil; 1H NMR (CDCl3) δ3.67 (m, 2H), 3.75 (s, 3H), 3.83 (m, 1H), 3.95 (m, 1H), 4.13 (m, 2H), 4.37 (m, 1H), 4.58 (m, 1H), 5.73 (dd, 1H), 5.86 (dd, 1H), 6.04 (dt, 1H), 6.17 (m, 1H), 6.40 (m, 1H), 6.58 (m, 1H), 6.9 (m, 4H) ppm.

Aufarbeitung

  1. customPurification on preparative reverse phase semi-prep column

Quellen und Nachweise

ORD-Eintrag
ord-c790d7a5ccd04d83b6196df5e563f7e4
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994346B2

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