Water → HCID 53738029, Verbindung

HRID 1081520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081520
[CH3:1][NH:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:14]([C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=1)[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1)[CH2:16][CH3:17].[Br-].[Br-].[Br-].B.O>C(Cl)Cl>[CH3:1][NH:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[C:15]([C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[CH2:16][CH3:17]

Komponenten

5

Edukt 3

HCID 962WaterHCID 54079109N-methyl-12,13-Bis(4-methoxyphenyl)-11-pentadecenoic amideHCID 178419136HCID 178419136, Verbindung

Produkt 1

HCID 53738029HCID 53738029, VerbindungAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the above dimethoxy amide 15 (117 mg, 0.22 mmol) in CH2Cl2 (1 ml) at 0° C. was added, under argon, 1.0 M borane tribromide (675 μl). The solution was stirred for 1 hour then poured into water and extracted with ether (3x). The organic solution was washed with water, dried on magnesium sulfate, and evaporated to dryness. The residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, unter 0.063 mm, 30 g). Elution with a mixture of hexane-ethyl acetate (4:1 v/v) gave N-butyl, N-methyl-12,13-Bis (4-hydroxyphenyl)-12-pentadecenoic amide ("EM-142", compound 16 with x=10) (34 mg, 31%), colorless oil, IR υmax (neat) 3300, 1600 cm-1 ; UV λmax (log ε)=235 (4.25) nm; 1H-NMR (δ, CDCl3), 0.76 (3H, t, J=7.3 Hz, --CH2CH3), 0.96 (3H, t,J=7.3 Hz, N (CH2)3CH3), 2.05-2.20 (4H, m, CH2 --C=C--CH2 --), 2.35 (2H, t,J=7.0 Hz, --CH2CON--), 2.97 and 3.00 (3H, s, --NCH3), 3.29 and 3.41 (2H, 2t, J=7.3 Hz --N--CH2 --), and 6.59-7.09 (8, m, H--Ar) ppm; MS m/e=493 (M+). ##STR23##

Aufarbeitung

  1. extractionextracted with ether (3x)
  2. washThe organic solution was washed with water
  3. customdried on magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by "Flash chromatography" on silica gel (Kieselgel 60, Merck, unter 0.063 mm, 30 g)
  6. washElution
  7. additionwith a mixture of hexane-ethyl acetate (4:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-25fec5e4f8c34a1b8717bdb3b749608e
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05585405

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