Triethylamine → 4-p-methoxyphenylbutyryl-L-prolinal dimethyl acetal

HRID 467150

Reaktionsgleichung

Reaktionsgleichung von HRID 467150
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.C(P(C#N)(CC)=O)C.C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.[CH:30]1C=CC=CC=1.[C:36]([O:39][CH2:40]C)(=[O:38])C>CN(C)C=O>[CH3:30][O:38][CH:36]([O:39][CH3:40])[C@@H:28]1[CH2:29][CH2:27][CH2:26][N:25]1[C:12](=[O:14])[CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 782804-(4-Methoxyphenyl)butyric acidHCID 13586794DiethylphosphorylcyanideHCID 21583983Benzene ethyl acetate

Produkt 1

HCID 151326394-p-methoxyphenylbutyryl-L-prolinal dimethyl acetalAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

L-prolinal dimethyl acetal hydrochloride obtained in the same manner as in Example 1 is dissolved in dimethylformamide (4 ml) containing 4-p-methoxyphenylbutyric acid (740 mg, 3.81 mmol) and diethylphosphoryl cyanide (0.48 ml, 3.16 mmol). To the solution is added dropwise triethylamine (1.15 ml, 8.25 mmol) under cooling and agitation in an ice-methanol bath. After the dropwise addition, the mixture is continued to be stirred for one hour under cooling and then for one hour at room temperature. Benzene-ethyl acetate (2:1, 150 ml) is added to the reaction mixture, and the organic layer is separated, washed successively with a saturated aqueous solution of sodium hydrogen carbonate (15 ml), water (15 ml) and a saturated aqueous solution of edible salt (15 ml), dried over sodium sulfate and filtered. The filtrate is concentrated to dryness under reduced pressure. The residue is purified by column chromatography on silica gel (benzene-ethyl acetate, 1:2→1:1) to give 727 mg (58%) of the title compound as white crystals.

Aufarbeitung

  1. temperatureunder cooling
  2. additionAfter the dropwise addition
  3. temperatureunder cooling
  4. waitfor one hour at room temperature
  5. customthe organic layer is separated
  6. washwashed successively with a saturated aqueous solution of sodium hydrogen carbonate (15 ml), water (15 ml)
  7. dry with materiala saturated aqueous solution of edible salt (15 ml), dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated to dryness under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel (benzene-ethyl acetate, 1:2→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-be129163bb1b45f48b3bb23d755404ea
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158970

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