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(R)-camphorsulfonic acid → HCID 86668042, Verbindung

HRID 474071
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 474071
[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([Br:16])[CH:11]=1)([CH2:8][OH:9])[CH2:6][OH:7])[CH3:2].[C@@:18]12(CS(O)(=O)=O)C(C)(C)C(C[CH2:24]1)C[C:19]2=O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([Br:16])[CH:11]=2)[CH2:8][O:9][C:18]([CH3:24])([CH3:19])[O:7][CH2:6]1)=[O:17])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 131278(R)-camphorsulfonic acidHCID 866680412-(2-Bromo-pyridin-4-yl)-3-hydroxy-2-hydroxymethyl-propionic acid ethyl ester

Produkt 1

HCID 86668042HCID 86668042, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-(2-bromo-pyridin-4-yl)-3-hydroxy-2-hydroxymethyl-propionic acid ethyl ester (30.0 g, 98.6 mmol) 2,2-dimethoxy propane (51.11 g, [60.5 ml], 493.1 mmol) and (1R)-(−)-10-camphor sulphonic acid (5.72 g, 24.65 mmol) in DMF (100 ml) was heated at 80° C. for 10 h. Reaction mixture was cooled to rt and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and worked up by washing with water, brine, followed by drying over anhy. Na2SO4. Organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography using 10% ethyl acetate in Hexane to obtain title compound as a yellow solid. Yield=18.15 g (53%). TLC (30% ethyl acetate in hexane) Rf=0.52; LCMS: RtH7=1.487; [M+1]+=344.0 and 346.0; HPLC RtH9=7.6 min (74%); 1H NMR (300 MHz, CDCl3): δ 8.41-8.34 (t, 1H), 7.54 (s, 1H), 7.32-7.28 (m, 1H), 4.51 (dd, 2H), 4.27-4.21 (q, 4H), 1.45 (s, 3H), 1.39 (s, 3H), 1.23 (t, 3H).

Aufarbeitung

  1. customReaction mixture
  2. temperaturewas cooled to rt
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washby washing with water, brine
  6. customby drying over anhy
  7. concentrationOrganic layer was concentrated under reduced pressure
  8. customthe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-da2d4b3427614812ba0ee24aa44478f7
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08637508B2

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