Iodobenzene diacetate → HCID 51356009, Verbindung

HRID 2367551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367551
[CH2:1]([C@H:3]1[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][C@@H:6]([CH2:16][OH:17])[O:5][CH2:4]1)[CH3:2].CC1(C)N([O])C(C)(C)CCC1.C(OI(C1C=CC=CC=1)OC(=O)C)(=[O:31])C>C(Cl)Cl>[CH3:14][C:12]([O:11][C:9]([N:8]1[C@H:3]([CH2:1][CH3:2])[CH2:4][O:5][C@H:6]([C:16]([OH:31])=[O:17])[CH2:7]1)=[O:10])([CH3:13])[CH3:15]

Komponenten

5

Edukt 3

HCID 76724Iodobenzene diacetateHCID 2724126TempoHCID 513540381,1-Dimethylethyl (2S,5R)-5-ethyl-2-(hydroxymethyl)-4-morpholinecarboxylate

Produkt 1

HCID 51356009HCID 51356009, VerbindungAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a vigorously stirred solution of 1,1-dimethylethyl(2S,5R)-5-ethyl-2-(hydroxymethyl)-4-morpholinecarboxylate (2.52 g, 10.27 mmol) in CH2Cl2 (50 mL) that was cooled to 0° C. were added TEMPO (0.321 g, 2.054 mmol) and (diacetoxyiodo)benzene (7.28 g, 22.60 mmol). The ice bath was removed, and the reaction was allowed to warm to room temperature and stirred overnight. The reaction was quenched with CH3OH and then concentrated to afford the title compound (0.711 g) as a yellow oil. LC-MS (ES) m/z=260 [M+H]+.

Aufarbeitung

  1. customThe ice bath was removed
  2. customThe reaction was quenched with CH3OH
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c18a34fdf2ce4983a38fbd76b9981f33
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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