Methyl (4R)-1,3,4,5,6,7,8,9,10,12-decahydro-16-hydroxy-14-methoxy-13-methyl-12-oxo-6-thioxo-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylate → HCID 54464536, Verbindung

HRID 234217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234217
C[O:2][C:3]([C@H:5]1[NH:18][C:17](=[S:19])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11](=[O:20])[C:10]2[C:21]([CH3:28])=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([OH:25])[C:9]=2[CH2:8][S:7][CH2:6]1)=O>CO.C(N)CC>[CH2:17]([NH:18][C:3]([C@H:5]1[NH:18][C:17](=[S:19])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11](=[O:20])[C:10]2[C:21]([CH3:28])=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([OH:25])[C:9]=2[CH2:8][S:7][CH2:6]1)=[O:2])[CH2:16][CH3:15]

Komponenten

4

Edukt 1

HCID 9823853Methyl (4R)-1,3,4,5,6,7,8,9,10,12-decahydro-16-hydroxy-14-methoxy-13-methyl-12-oxo-6-thioxo-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylate

Produkt 1

HCID 54464536HCID 54464536, VerbindungAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 7852PropylamineLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 43 mg of the product of Example 23 in a mixture of 0.5 ml of methanol and 0.5 ml of propylamine was heated to 50° C. for 6 h. The solution was evaporated in vacuo, the residue was dissolved in ethyl acetate and the solution was washed with 1N hydrochloric acid and water. The organic layer was dried over sodium sulfate and evaporated in vacuo, the residue was chromatographed on silica gel using ethyl acetate/hexane (1:2, v/v) as eluent, and the purified product was crystallized from ethyl acetate/hexane to afford 22 mg of (R)-16-hydroxy-14-methoxy-13-methyl-12-oxo-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylic acid propylamide as a white solid.

Aufarbeitung

  1. customThe solution was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution was washed with 1N hydrochloric acid and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customthe residue was chromatographed on silica gel
  7. customv/v) as eluent, and the purified product was crystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ace809e2b1ff4e3585639cda64c9772b
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594135

Notizen zur Reaktion

Wird geladen…