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Chloromethyl Methyl Ether → benzyl (2S*,3R*)-5-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-2-(3,4,5-trifluorophenyl)pentanoate

HRID 546685
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Reaktionsgleichung

Reaktionsgleichung von HRID 546685
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][CH2:12]Cl.[Si:14]([O:31][CH2:32][CH2:33][C@@H:34]([OH:55])[C@H:35]([C:46]1[CH:51]=[C:50]([F:52])[C:49]([F:53])=[C:48]([F:54])[CH:47]=1)[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCCl>[Si:14]([O:31][CH2:32][CH2:33][C@@H:34]([O:55][CH2:10][O:11][CH3:12])[C@H:35]([C:46]1[CH:51]=[C:50]([F:52])[C:49]([F:53])=[C:48]([F:54])[CH:47]=1)[C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 66838983benzyl (2S*,3R*)-5-(tert-butyldiphenylsilanyloxy)-3-hydroxy-2-(3,4,5-trifluorophenyl)pentanoate

Produkt 1

HCID 66838992benzyl (2S*,3R*)-5-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-2-(3,4,5-trifluorophenyl)pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

IPEA (0.742 mL) and chloromethyl methyl ether (0.324 mL) were added to a solution of benzyl (2S,3R)-5-(tert-butyldiphenylsilanyloxy)-3-hydroxy-2-(3,4,5-trifluorophenyl)pentanoate (840 mg) in 1,2-dichloroethane (20 mL) at 0° C. The reaction solution was stirred at 60° C. for 4 hours and then left to cool to room temperature and concentrated under reduced pressure. Ethyl acetate and a saturated ammonium chloride solution were added to the residue, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 875 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. waitleft
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionEthyl acetate and a saturated ammonium chloride solution were added to the residue
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-eac8bdf989494725bedcd3234929b53b
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935815B2

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