Hydrochloric Acid → HCID 44349654, Verbindung

HRID 5423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 5423
C([S:4][CH2:5][CH:6]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][CH2:10][C@@H:9]([C:20]([O:22]CC2C=CC=CC=2)=[O:21])[NH:8][C:7]1=[O:30])(=O)C.O.[OH-].[Li+].Cl>>[SH:4][CH2:5][CH:6]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][CH2:10][C@@H:9]([C:20]([OH:22])=[O:21])[NH:8][C:7]1=[O:30]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 44349442Benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylate

Produkt 1

HCID 44349654HCID 44349654, Verbindung

Versuchsvorschrift

Benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylate (Isomer A), (0.11 g, 0.25 mmol) is dissolved in nitrogen degassed tetrahydrofuran (5 ml) and water (1 ml). Lithium hydroxide monohydrate (0.032 g, 0.75 mmol) is added and the mixture is stirred for 3 hours at room temperature. The mixture is poured into 1N hydrochloric acid and extracted with ethyl acetate (2×50 ml). The combined organic layers are washed with brine (1×50 ml), dried (MgSO4) and the solvent is evaporated. The product is triturated from diethyl ether/hexane (1:1) to give (3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylic acid (Isomer A), m.p. 165°-168° C.

Aufarbeitung

  1. customdegassed tetrahydrofuran (5 ml) and water (1 ml)
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. washThe combined organic layers are washed with brine (1×50 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent is evaporated
  6. customThe product is triturated from diethyl ether/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-87d288d6baf14569856e62b2735e05e2
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244889

Notizen zur Reaktion

Wird geladen…