Triethylamine → Ether methanol ammonium hydroxide

HRID 1270436

Reaktionsgleichung

Reaktionsgleichung von HRID 1270436
[CH2:1]([N:3]([CH2:6][CH3:7])CC)C.Br[CH2:9][CH2:10]NS(C)(=O)=[O:13].[OH-:16].[Na+]>CN(C=O)C>[CH3:9][CH2:10][O:16][CH2:6][CH3:7].[CH3:1][OH:16].[OH-:13].[NH4+:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 285330N-(2-bromoethyl)methanesulfonamide

Produkt 1

HCID 131726330Ether methanol ammonium hydroxideAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of compound (AFD) (0.40 mmol) in dry DMF was added triethylamine (0.45), followed by the alkylating agent Br(CH2)2NHSO2CH3 (0.45 mmol). The resulting mixture was stirred at 80° C. overnight. After completion of the reaction, the cooled mixture was poured into 1M NaOH (150 mL) and extracted with ethyl acetate (2×100 mL). The organic extracts were dried (MgSO4) and the solvent evaporated at the rotary evaporator to leave a gum. Flash chromatography of the residue (SiO2, ether:methanol:ammonium hydroxide (200:10:1)) provided compound (AFV) as a colorless gum: (yield:26%); purity >97% (HPLC); MS: m/z 616.3 (M+1); 1H NMR (DMSO d6): δ 2.1–2.2 (br s, 3H), 2.3–2.4 (m, 5H), 2.75 (s, 3H) 2.9–2.10 (br s, 3H), 3.3–3.4 (m, 6H), 3.5 (m, 3H), 4.65 (m, 2H), 7.15–7.5 (m, 16H).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. customthe solvent evaporated at the rotary evaporator
  5. customto leave a gum

Quellen und Nachweise

ORD-Eintrag
ord-7f259a7924fd41cca8357dc53868666d
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202259B2

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