Hydrochloric Acid → trans 3-Mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxamide

HRID 5397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 5397
C([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([NH2:18])=[O:17])[NH:8][C:7]1=[O:19])(=O)C.[OH-].[Na+].Cl>C(O)C>[SH:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([NH2:18])=[O:17])[NH:8][C:7]1=[O:19]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86747204trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

Produkt 1

HCID 86747205trans 3-Mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide (0.16 g, 0.56 mmol) is dissolved in ethanol (5.0 mL). An aqueous solution of 1N sodium hydroxide (0.60 mL, 0.60 mmol) is added, and the reaction is stirred for 1 hour. The reaction is acidified with 1N hydrochloric acid to a pH of about 3, and the solvent is evaporated. The residue is partitioned between ethyl acetate and water, and the aqueous layer is extracted several times with ethyl acetate. The combined organic layers are dried (Na2SO4), and the solvent is evaporated to give trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxamide, m.p. 185°-192° C.

Aufarbeitung

  1. customthe solvent is evaporated
  2. customThe residue is partitioned between ethyl acetate and water
  3. extractionthe aqueous layer is extracted several times with ethyl acetate
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b118b628f60746c29335fc3e59194550
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244889

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