Acetic Acid → HCID 44594157, Verbindung

HRID 1099512

Reaktionsgleichung

Reaktionsgleichung von HRID 1099512
[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:9]([CH2:12][CH2:13][CH3:14])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]1([N+:25]#[C-:26])[CH2:24][CH2:23]1.[C:27](O)(=[O:29])[CH3:28].C(=O)(O)[O-:32].[Na+]>ClCCl.CCCCCC>[C:27]([O:11][C@@H:10]([C@@H:9]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:12][CH2:13][CH3:14])[C:26]([NH:25][CH:22]1[CH2:24][CH2:23]1)=[O:32])(=[O:29])[CH3:28]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2758008IsocyanocyclopropaneHCID 44223341(S)-2-(dibenzylamino)pentanal

Produkt 1

HCID 44594157HCID 44594157, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

To a cooled (0-5° C.) solution of (S)-2-(dibenzylamino)pentanal in dichloromethane (210 mL) was added cyclopropylisonitrile followed by acetic acid at 0-5° C. The reaction mixture temperature was raised to 25-30° C. over 40-60 minutes, and stirred for 16-18 hours at 25-30° C. Progress of the reaction was monitored by TLC analysis. When the reaction was complete, the mixture was cooled to 0-5° C., and saturated sodium bicarbonate solution (200 mL) was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane twice. The combined organic layers were washed with water (1×200 mL), brine (1×200 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product thus obtained was slurried in hexane (150 mL) and stirred for one hour at 25-35° C. The slurry was filtered and the solid washed with hexane and dried under reduced pressure to provide 17.0 g of (2S,3S)-1-(cyclopropylamino)-3-(dibenzylamino)-1-oxohexan-2-yl acetate as a white solid.

Aufarbeitung

  1. temperaturethe mixture was cooled to 0-5° C.
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane twice
  4. washThe combined organic layers were washed with water (1×200 mL), brine (1×200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product thus obtained
  8. stirringstirred for one hour at 25-35° C
  9. filtrationThe slurry was filtered
  10. washthe solid washed with hexane
  11. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-17fb77a7952b41eab4f32262ae1b570a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143448B2

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