Hydrochloric Acid → HCID 67926517, Verbindung

HRID 981257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 981257
[C:1]([C:4]1[CH:44]=[CH:43][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([S:27][C:28]3[CH:33]=[CH:32][C:31]([C:34](=[O:42])[CH:35]([CH3:41])[CH2:36][C:37]([O:39]C)=[O:38])=[CH:30][CH:29]=3)[CH:20]([CH3:26])[CH2:21][C:22]([O:24]C)=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:45][CH2:46][CH3:47])[C:5]=1[OH:48])(=[O:3])[CH3:2].CO.[OH-].[Na+].Cl>C1COCC1.O>[OH2:3].[C:1]([C:4]1[CH:44]=[CH:43][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([S:27][C:28]3[CH:29]=[CH:30][C:31]([C:34](=[O:42])[CH:35]([CH3:41])[CH2:36][C:37]([OH:39])=[O:38])=[CH:32][CH:33]=3)[CH:20]([CH3:26])[CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:45][CH2:46][CH3:47])[C:5]=1[OH:48])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 20071763HCID 20071763, Verbindung

Produkt 1

HCID 67926517HCID 67926517, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ester from Step A of this Example (760 mg) in THF (15 ml) and MeOH (1 ml) was added 2N NaOH (2.4 ml) and stirred overnight at room temperature. The reaction mixture was diluted with H2O (50 ml) and acidified with 2N HCl and extracted with CH2Cl2 (2×50 ml). The combined organic layers were washed with brine, dried over Na2SO4 and purified on a column of flash silica gel 230-400 mesh using toluene-dioxane-acetic acid (10:2:0.1) as eluant to give the title compound as a foam (580 mg, 79%).

Aufarbeitung

  1. extractionextracted with CH2Cl2 (2×50 ml)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. custompurified on a column of flash silica gel 230-400 mesh

Quellen und Nachweise

ORD-Eintrag
ord-3e4ff46650eb4d4c93f9ead754d97bb9
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990526

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