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Acetic Anhydride → (3R,4S,5R,6R)-6-(acetoxymethyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl

HRID 2172700
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2172700
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][C:14]3[CH:15]=[C:16]([C:21]4([O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]4[OH:25])[O:22][CH3:23])[CH:17]=[CH:18][C:19]=3[CH3:20])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN1[CH2:40][CH2:39][O:38]CC1.C(O[C:45](=[O:47])[CH3:46])(=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[C:21]([O:25][C@@H:24]1[C@@H:26]([O:27][C:24](=[O:25])[CH3:26])[C@H:28]([O:29][C:45](=[O:47])[CH3:46])[C@@H:30]([CH2:32][O:33][C:39](=[O:38])[CH3:40])[O:31][C:21]1([C:16]1[CH:17]=[CH:18][C:19]([CH3:20])=[C:14]([CH2:13][C:11]2[S:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[CH:15]=1)[O:22][CH3:23])(=[O:22])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 7918Acetic AnhydrideHCID 79724-MethylmorpholineHCID 46930624(3R,4S,5S,6R)-2-(3-((5-(4-Fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Produkt 1

HCID 46899467(3R,4S,5R,6R)-6-(acetoxymethyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucopyranoside (net weight 10.54 g) in toluene and ethyl acetate was added N-methylmorpholine (11.9 g) and 4-dimethylaminopyridine (217 mg) at room temperature. The solution was cooled to 0° C. and acetic anhydride (52.7 mL) was added dropwise below 15° C. The reaction mixture was allowed to warm to room temperature and stirred for 15 hours. The mixture was quenched with 28% NH3 aqueous solution (ca. 31.6 mL) while maintaining pH range of 6 to 7. Water was added to the mixture and separated. The organic layer was washed with water and brine, dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to give methyl 2,3,4,6-tetra-O-acetyl-1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucopyranoside (17.59 g) as yellow oil.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customThe mixture was quenched with 28% NH3 aqueous solution (ca. 31.6 mL)
  3. temperaturewhile maintaining pH range of 6 to 7
  4. additionWater was added to the mixture
  5. customseparated
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bd5555f8abf44beabf098562749ed52b
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09056850B2

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