Hydrochloric Acid → HCID 54137898, Verbindung

HRID 620792

Reaktionsgleichung

Reaktionsgleichung von HRID 620792
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH2:21][OH:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:24][C:25]([OH:27])=[O:26].[OH-].[K+].[I-].[K+].Cl.[Cl-].[Na+]>C(O)(C)(C)C.O>[C:17]([O:16][C:14]([N:12]1[CH2:13][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][C@H:11]1[CH2:21][O:22][CH2:24][C:25]([OH:27])=[O:26])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 6227Bromoacetic AcidHCID 14797Potassium HydroxideHCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 54137898HCID 54137898, VerbindungAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of (2S,4R)-4-t-butyldimethylsilyloxy-1-t-butoxycarbonyl-2-(hydroxymethyl)pyrrolidine (0.62 g), 2-bromoacetic acid (0.26 g), 85% potassium hydroxide (0.37 g), and potassium iodide (0.93 g) in t-butyl alcohol (12 ml) was heated at 50° C. for 3 hours. The mixture was poured into water (100 ml), adjusted to pH 4 with 1N hydrochloric acid and saturated with sodium chloride. The aqueous mixture was extracted with three 50 ml portions of ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (30 g ) eluting with a mixture of methanol and dichloromethane (1:9 V/V) to give (2S,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-(carboxymethyloxymethyl)pyrrolidine (0.57 g).

Aufarbeitung

  1. extractionThe aqueous mixture was extracted with three 50 ml portions of ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (30 g )
  6. washeluting with a mixture of methanol and dichloromethane (1:9 V/V)

Quellen und Nachweise

ORD-Eintrag
ord-cca902987ef84e6990b3784a70923176
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04822787

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