Cesium carbonate → HCID 67508125, Verbindung

HRID 1770684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1770684
[SH:1][CH2:2][CH2:3][C:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:6])[CH3:5].[O:18]1[CH2:20][CH:19]1[CH2:21][OH:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[OH:18][CH:19]([CH2:21][OH:22])[CH2:20][S:1][CH2:2][CH2:3][C:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 11164GlycidolHCID 86665509Benzyl 4-mercapto-2-methylbutan-2-ylcarbamate

Produkt 1

HCID 67508125HCID 67508125, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of benzyl 4-mercapto-2-methylbutan-2-ylcarbamate (3.04 g, 12.0 mmol) in N,N-dimethylformamide (50 ml) was added oxiran-2-ylmethanol (1.10 ml, 16.6 mmol) and cesium carbonate (520 mg, 1.6 mmol). The solution was heated to 85° C. for 16 hour, cooled to room temperature, and concentrated in vacuo. The residue was purified by flash chromatography (30% to 80% ethyl acetate in hexanes) to afford the title compound as a clear oil (3.52 g, 10.8 mmol, 90%). 1H NMR (400 MHz, CDCl3) δ 1.30 (m, 6H), 2.0-2.1 (m, 2H), 2.24 (m, 1H), 2.49-2.62 (m, 3H), 2.71 (m, 1H), 3.5 (m, 1H), 3.7 (m, 2H), 4.75 (s, 1H), 5.06 (s, 2H), 7.3-7.4 (m, 5H); LRMS (ESI/APCI) m/z 328 [M+H]+, 350 [M+Na]+.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography (30% to 80% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fb67f0deaacd448d837fa125f3fae9f0
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09248117B2

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