Hydrochloric Acid → Methyl 4-(acetylamino)-1-cyclopentene-1-carboxylate

HRID 728659

Reaktionsgleichung

Reaktionsgleichung von HRID 728659
[C:1]([NH:4][C@@H:5]1[CH2:9][C@H:8]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:6]1)(=[O:3])[CH3:2].C[O-].[Na+].[Na].Cl>CO>[C:1]([NH:4][CH:5]1[CH2:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH2:6]1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 361509(1R,4S)-rel-4-(Acetylamino)-2-cyclopentene-1-carboxylic Acid Methyl EsterHCID 5360545SodiumHCID 10942334Sodium Methoxide

Produkt 1

HCID 19822736Methyl 4-(acetylamino)-1-cyclopentene-1-carboxylateAusbeute 111 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

(±)-cis-Methyl 4-acetamido-2-cyclopentene 1-carboxylate [S. Daluge and R. Vince, J. Org. Chem. 1978. 43, 2311](3.90 g, 21.3 mmol) was dissolved in dry methanol (25 mL) and added to a solution of sodium methoxide prepared from sodium (0.98 g, 43 m.equiv.) and dry methanol (150 mL). This solution was stirred at 25° C. for 2.0 hours and then neutralized with 1 N hydrochloric acid. The solution was concentrated to 40 mL and extracted with chloroform (3×75 mL). The chloroform was dried (MgSO4) and evaporated to colourless glass (3.9 g). Chromatography on silica gel with 1-2% methanol-chloroform gave title compound as white crystals (4.33 g, 82%); m.p. 72-74° C [Lit. Can. J. Chem. 1985 63, 2787; m.p. 75-76° C. Sublimation of such a sample at 100°/0.2 mm gave white crystals, m.p. 72-74° C.

Aufarbeitung

  1. concentrationThe solution was concentrated to 40 mL
  2. extractionextracted with chloroform (3×75 mL)
  3. dry with materialThe chloroform was dried (MgSO4)
  4. customevaporated to colourless glass (3.9 g)

Quellen und Nachweise

ORD-Eintrag
ord-a15b8ee984b3436a89f9b64354a1dd1b
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05049671

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