Acetyl chloride → trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

HRID 21967

Reaktionsgleichung

Reaktionsgleichung von HRID 21967
[SH:1][CH2:2][C@H:3]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([C:13]([OH:15])=[O:14])[NH:5][C:4]1=[O:16].[C:17](Cl)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([S:1][CH2:2][C@H:3]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([C:13]([OH:15])=[O:14])[NH:5][C:4]1=[O:16])(=[O:19])[CH3:18]

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 86747203Trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxylic acid

Produkt 1

HCID 86747202trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxylic acid (0.75 g, 3.06 mmol) is dissolved in pyridine (20 mL). Acetyl chloride (0.26 g, 3.37 mmol) is added, and the reaction is stirred at room temperature overnight. The reaction is quenched by cooling to 0° C., adding concentrated hydrochloric acid (20 mL), diluting with water, and extracting several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated to give trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid, MS: M+1=288.

Aufarbeitung

  1. customThe reaction is quenched
  2. temperatureby cooling to 0° C.
  3. additionadding concentrated hydrochloric acid (20 mL)
  4. additiondiluting with water
  5. extractionextracting several times with ethyl acetate
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-59dc5b80135948aba5d46d8e397c7604
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426103

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