Acetic Acid → HCID 57228158, Verbindung

HRID 703579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 703579
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][O:24][CH2:25][C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])[CH2:6]1)(=O)C.[H-].[Na+].C(O)(=O)C>C(O)C=C.C(OCC)(=O)C>[CH2:29]([O:28][C:26]([CH2:25][O:24][CH2:23][C@@H:7]1[CH2:6][C@H:5]([SH:4])[CH2:9][N:8]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11])=[O:27])[CH:30]=[CH2:31]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 57063209(2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Produkt 1

HCID 57228158HCID 57228158, VerbindungAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7858Allyl AlcoholLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2S,4S)-4-acetylthio- 2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (4.25 g) in allyl alcohol (40 ml) was added sodium hydride (62.8% in oil suspension) (0.5 g) at -5°~0° C. in a nitrogen stream. After stirring for 1 hour, acetic acid (1 ml) was added to the mixture. The mixture was concentrated under reduced pressure to give a syrup. The syrup was dissolved in ethyl acetate (50 ml), washed in turn with water (50 ml) and brine (50 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (30 g) and eluted with chloroform to give (2S,4S)-2-(allyloxycarbonylmethyloxymethyl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.29 g).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a syrup
  3. washwashed in turn with water (50 ml) and brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-c24ec7255c0f4ce0a9f85bcf8a1d1f78
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04983596

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