Water → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxide

HRID 1776555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776555
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:50])[CH:5]=[C:6]([Cl:49])[C:7]=1[CH2:8][C@@H:9]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]2[CH2:48][CH2:47]2)[CH:35]=1)[O:10][C:11](=[O:33])[CH2:12][O:13]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>C(Cl)Cl.Br>[Cl:49][C:6]1[CH:5]=[N+:4]([O-:50])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]2[CH2:48][CH2:47]2)[CH:35]=1)[O:10][C:11](=[O:33])[CH2:12][OH:13]

Komponenten

5

Edukt 2

HCID 962WaterHCID 86679511(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(trityloxy)acetoxy)ethyl)pyridine 1-oxide

Produkt 1

HCID 86679512(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 260Hydrogen BromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(trityloxy)acetoxy)ethyl)pyridine 1-oxide (4.0 g, 5.55 mmol) in DCM (1 Lt) cooled at 0° C., 160 drops of 48% HBr were added, and the reaction was stirred for 1 hour (temperature below 10° C.). Water was added to the mixture, the organic phase was separated, dried over Na2SO4 and evaporated under vacuum (bath temperature=25° C.). The crude compound was dissolved in DCM, and hexanes was added. The white precipitate thus formed was filtered and washed with plenty of hexanes. After drying, (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxide was obtained (2.26 g, 4.73 mmol, 76% yield, MS/ESI+ 478.0 [MH]+) and used in the following step without further purification.

Aufarbeitung

  1. customthe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum (bath temperature=25° C.)
  4. dissolutionThe crude compound was dissolved in DCM
  5. additionhexanes was added
  6. customThe white precipitate thus formed
  7. filtrationwas filtered
  8. washwashed with plenty of hexanes
  9. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-491b4fc5663d43ed82d4d519a36de860
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265768B2

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