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Triethylamine → (4S,5S)-4-((tert-Butyldiphenylsilyloxy)methyl)-5-phenyloxazolidin-2-one

HRID 929944
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 929944
[OH:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][C:5](=[O:14])[NH:4]1.CCN(CC)CC.[CH3:22][C:23]([Si:26](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])[CH3:24]>CN(C1C=CN=CC=1)C.CN(C=O)C>[Si:26]([O:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][C:5](=[O:14])[NH:4]1)([C:23]([CH3:25])([CH3:24])[CH3:22])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 11116891(4S,5S)-4-Hydroxymethyl-5-phenyl-oxazolidin-2-one

Produkt 1

HCID 86718526(4S,5S)-4-((tert-Butyldiphenylsilyloxy)methyl)-5-phenyloxazolidin-2-oneAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (4S,5S)-4-hydroxymethyl-5-phenyl-oxazolidin-2-one (3.50 g, 17.2 mmol), NEt3 (4.80 mL, 34.4 mmol), and DMAP (105 mg, 861 μmol) in DMF (20 mL) was added dropwise TBDPSCl (4.86 mL, 18.9 mmol) at room temperature. The reaction was stirred for 3 hours at room temperature. The reaction mixture was then concentrated and diluted with TBME, the organic layers were separated, washed with aqueous NaHCO3 and brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography (120 g SiO2) using EtOAc in heptane from 0% to 60% in order to give the title compound as a white solid (4.28 g, 57%). LC-MS: [M+H] 432.2; Rt 1.36 min; (LCMS method 2).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with TBME
  3. customthe organic layers were separated
  4. washwashed with aqueous NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (120 g SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-4f470b8dd2a4424da64fa65619ff1c39
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296733B2

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