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HCID 54419005, Verbindung → (11S)-N-hydroxy-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanamide

HRID 849728
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 849728
C([O:8][NH:9][C:10](=[O:41])[CH2:11][CH:12]([C:17](=[O:40])[NH:18][C@H:19]1[CH2:37][C:36]2=[CH:38][N:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=32)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]1=[O:39])[CH2:13][CH:14]([CH3:16])[CH3:15])C1C=CC=CC=1.[H][H]>C(O)C.O1CCCC1.[Pd]>[OH:8][NH:9][C:10](=[O:41])[CH2:11][CH:12]([C:17](=[O:40])[NH:18][C@H:19]1[CH2:37][C:36]2=[CH:38][N:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=32)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]1=[O:39])[CH2:13][CH:14]([CH3:16])[CH3:15]
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Komponenten

5

Edukt 2

HCID 54419005HCID 54419005, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86752867(11S)-N-hydroxy-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21873804
Tetrahydrofuran ethanol
Lösungsmittel

Versuchsvorschrift

To a solution of the more polar stereoisomer of (11S)-N-benzyloxy-5-methyl-3-(10-oxo-1,9-diazatricyclo-[11.6.1.014,19 ]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanamide (90 mg) in ethanol/tetrahydrofuran (350 mL; 2:1) was added 10% palladium on charcoal (30 mg). The material was stirred with a constant stream of hydrogen gas bubbling through it. After 3 hours TLC (10% CH3OH/CH2Cl2) showed the reaction was complete. The material was filtered through a bed of celite (3X) and concentrated under reduced pressure to an almost dry residue. Methylene chloride (15 mL) was added and the material was again concentrated under reduced pressure until almost dried and then repeated. To the residue was added 3-4 drops of methanol followed by methylene chloride (15 mL). The material was stirred with cooling (ice bath) and ether (5 mL) and then hexane (2 mL) was added. A crystalline material slowly emerged and was collected by filtration to yield 50 mg of the more polar stereoisomer of (11S)-N-hydroxy-5-methyl-3-(10-oxo-1,9-diazatricyclo-[11.6.1.014,19 ]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanamide, m.p. 197-201° C., [α]D23 =-85.1° (3.5 mg/1.0 mL DMSO).

Aufarbeitung

  1. custombubbling through it
  2. filtrationThe material was filtered through a bed of celite (3X)
  3. concentrationconcentrated under reduced pressure to an almost dry residue
  4. additionMethylene chloride (15 mL) was added
  5. concentrationthe material was again concentrated under reduced pressure
  6. customuntil almost dried
  7. additionTo the residue was added 3-4 drops of methanol
  8. temperaturewith cooling (ice bath) and ether (5 mL)
  9. additionhexane (2 mL) was added
  10. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a844ad5c2a244995951fb15d1d8e2855
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06013792

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