HCID 69391299, Verbindung → HCID 69385752, Verbindung

HRID 916806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916806
[CH3:1][C:2]1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16]C(=O)[N:14]([CH2:18][CH2:19][C:20]4[CH:44]=[CH:43][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]5[CH:30]=[C:31]([NH:35][C:36]([C:38]6[O:39][CH:40]=[CH:41][CH:42]=6)=[O:37])[CH:32]=[CH:33][CH:34]=5)=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.O([Si](C)(C)C)[K]>C1COCC1>[C:2]([OH:7])(=[O:3])[CH3:1].[OH:16][C@H:12]([C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([CH2:4][OH:3])[CH:11]=1)[CH2:13][NH:14][CH2:18][CH2:19][C:20]1[CH:44]=[CH:43][C:23]([O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]2[CH:30]=[C:31]([NH:35][C:36]([C:38]3[O:39][CH:40]=[CH:41][CH:42]=3)=[O:37])[CH:32]=[CH:33][CH:34]=2)=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 69391299HCID 69391299, VerbindungHCID 178504318HCID 178504318, Verbindung

Produkt 1

HCID 69385752HCID 69385752, VerbindungAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

N-(3-{[2-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}phenyl)-2-furamide (34 mg) in THF (2 mL) was treated with KOSiMe3 (18 mg) and the resulting solution was heated at 75° C. for 4 h. The reaction mixture was then quenched with MeOH and concentrated in vacuo. The residue was then purified by HPLC, before dissolving in acetic acid (1 mL) and water (0.33 mL) and heating at 75° for 20 min. The solution was then concentrated in vacuo and azeotroped with MeOH to give the title compound (3.4 mg). LCMS RT=2.45 min. ES+ve 547 (MH)+

Aufarbeitung

  1. customThe reaction mixture was then quenched with MeOH
  2. concentrationconcentrated in vacuo
  3. customThe residue was then purified by HPLC
  4. dissolutionbefore dissolving in acetic acid (1 mL)
  5. temperaturewater (0.33 mL) and heating at 75° for 20 min
  6. concentrationThe solution was then concentrated in vacuo
  7. customazeotroped with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-2e8bfa522a32462f8331652d4b2323c1
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271197B2

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