Hydrochloric Acid → trans N-[[(3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotridecan-3-yl]-carbonyl]-4-hydroxy-L-proline

HRID 21995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21995
C([O:8][C:9](=[O:40])[C@@H:10]1[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]1[C:16]([C@H:18]1[NH:30][C:29](=[O:31])[CH:28]([CH2:32][S:33]C(=O)C(C)(C)C)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][S:20][CH2:19]1)=[O:17])C1C=CC=CC=1.O.[OH-].[Li+].Cl>>[SH:33][CH2:32][CH:28]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][S:20][CH2:19][C@@H:18]([C:16]([N:11]2[CH2:12][C@H:13]([OH:15])[CH2:14][C@H:10]2[C:9]([OH:40])=[O:8])=[O:17])[NH:30][C:29]1=[O:31]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 54096127Trans-N-[(3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecan-3-yl-carbonyl]-4-hydroxy-L-proline benzyl ester

Produkt 1

HCID 53825878trans N-[[(3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotridecan-3-yl]-carbonyl]-4-hydroxy-L-proline

Versuchsvorschrift

Trans-N-[(3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecan-3-yl-carbonyl]-4-hydroxy-L-proline benzyl ester (0.30 g, 0.05 mmol) is dissolved in nitrogen degassed tetrahydrofuran (1 ml) and water (0.5 ml). Lithium hydroxide monohydrate (0.006 g, 0.15 mmol) is added and the mixture is stirred at room temperature for 2.5 hours. The mixture is poured into 1N hydrochloric acid and extracted with ethyl acetate (2×10 ml). The combined organic layers are dried (MgSO4) and the solvent is evaporated. The product is triturated from diethyl ether to give trans N-[[(3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotridecan-3-yl]-carbonyl]-4-hydroxy-L-proline, m.p. 124°-130° C.

Aufarbeitung

  1. customdegassed tetrahydrofuran (1 ml) and water (0.5 ml)
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. customthe solvent is evaporated
  5. customThe product is triturated from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-49a71dae419145bb85402cdaff07ddf2
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426103

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