Benzyl succinimido carbonate → HCID 86705287, Verbindung

HRID 879231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879231
C(OC([NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C@@H:18]1[CH2:27][C@H:26]([CH3:28])[C:21]2([O:25][CH2:24][CH2:23][O:22]2)[C@H:20]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:19]1)=O)C1C=CC=CC=1.C(ON1C(=O)CCC1=O)(OCC1C=CC=CC=1)=O>CO.C(Cl)Cl.CCOC(C)=O.[Pd]>[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C@H:18]1[CH2:27][C@@H:26]([CH3:28])[C:21]2([O:22][CH2:23][CH2:24][O:25]2)[C@@H:20]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:19]1.[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C@@H:18]1[CH2:27][C@H:26]([CH3:28])[C:21]2([O:22][CH2:23][CH2:24][O:25]2)[C@H:20]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:19]1

Komponenten

8

Edukt 2

HCID 83172Benzyl succinimido carbonateHCID 86705285HCID 86705285, Verbindung

Produkt 2

HCID 86705287HCID 86705287, VerbindungAusbeute 28 %HCID 86705288HCID 86705288, VerbindungAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(+/−)-Benzyl ((6R,8R,10S)-8-(3-((benzoxycarbonyl)amino)pyridin-4-yl)-10-methyl-1,4-dioxaspiro[4.5]decan-6-yl)carbamate (1.0 equiv.) was dissolved in MeOH (0.10 M) and degassed with Argon to vacuum. Pd/C (0.05 equiv.) was added and the mixture was stirred under a H2 balloon for 20 hrs. The mixture was filtered and concentrated. The crude and CBZ-OSu (0.99 equiv.) were dissolved in DCM (0.20 M). The reaction was stirred at room temperature for 2 hrs. The solution was diluted with EtOAc and washed with water, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by ISCO chromatography. Purification was completed via SFC (40% EtOH, 15 mL/min, OJ column) to yield benzyl (6S,8S,10R)-8-(3-aminopyridin-4-yl)-10-methyl-1,4-dioxaspiro[4.5]decan-6-ylcarbamate (28% yield, 99% ee) and benzyl (6R,8R,10S)-8-(3-aminopyridin-4-yl)-10-methyl-1,4-dioxaspiro[4.5]decan-6-ylcarbamate (13% yield, 99% ee). LC/MS (m/z)=398.2 (MH+), Rt=0.64 min.

Aufarbeitung

  1. customdegassed with Argon to vacuum
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. stirringThe reaction was stirred at room temperature for 2 hrs
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by ISCO chromatography
  10. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-eceac986632d41a7bb343726575e297b
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987457B2

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