L-Pyroglutamic Acid → HCID 86626712, Verbindung

HRID 1474581

Reaktionsgleichung

Reaktionsgleichung von HRID 1474581
[NH:1]1[C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3][C:2]1=[O:9].[OH-].[CH2:11]([P+:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>CO>[NH:1]1[C@H:5]([C:6]([O-:8])=[O:7])[CH2:4][CH2:3][C:2]1=[O:9].[CH2:24]([P+:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:25][CH2:26][CH3:27]

Komponenten

4

Edukt 2

HCID 7405L-Pyroglutamic AcidHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

Produkt 1

HCID 86626712HCID 86626712, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

5.0 g of (S)-(−)-2-pyrrolidone-5-carboxylic acid (by Wako Pure Chemical Industries) was suspended in 30 ml of methanol, and 26.8 g of aqueous 40% tetrabutylphosphonium hydroxide (by Aldrich) was dropwise added thereto at 0° C., taking 3 minutes. After being stirred for 10 minutes, this was concentrated under reduced pressure at 40° C., using an evaporator. 50 ml of methanol was added to the residue, and the mixture was concentrated under reduced pressure in the same manner. 100 ml of toluene was added to the obtained residue, and the resulting mixture was concentrated under reduced pressure; and this operation was repeated twice. Next, this was concentrated in ultra-high vacuum at from room temperature to 50° C. for 15 hours. 15.3 g of tetrabutylphosphonium (S)-(−)-2-pyrrolidone-5-carboxylate (purity, 98.0%) was obtained as an oily compound. (This is an ionic liquid A.) In NMR analysis, neither toluene nor methanol was detected.

Aufarbeitung

  1. concentrationthis was concentrated under reduced pressure at 40° C.
  2. customan evaporator
  3. addition50 ml of methanol was added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure in the same manner
  5. addition100 ml of toluene was added to the obtained residue
  6. concentrationthe resulting mixture was concentrated under reduced pressure
  7. concentrationNext, this was concentrated in ultra-high vacuum at from room temperature to 50° C. for 15 hours

Quellen und Nachweise

ORD-Eintrag
ord-6454a0abcdf64cf5b9d29773a389a8cc
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018321B2

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