(3S,6S,7R,8R)-3-[[(3-Hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl 2-methylpropanoate → N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide

HRID 1071006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071006
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C@@H:12]1[O:22][C:20](=[O:21])[C@@H:19]([NH:23][C:24]([C:26]2[C:31]([OH:32])=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)=[O:25])[CH2:18][O:17][C:15](=[O:16])[C@H:14]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:13]1[O:42]C(C(C)C)=O>C1(C)C=CC=CC=1>[CH2:35]([C@@H:14]1[C@@H:13]([OH:42])[C@H:12]([CH3:11])[O:22][C:20](=[O:21])[C@@H:19]([NH:23][C:24]([C:26]2[C:31]([OH:32])=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)=[O:25])[CH2:18][O:17][C:15]1=[O:16])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Komponenten

4

Edukt 2

HCID 468590(3S,6S,7R,8R)-3-[[(3-Hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl 2-methylpropanoateHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 11236123N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamideAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Diisobutylaluminum hydride (1.5 M in toluene, 23.3 mmol) was added dropwise to a 15° C. solution of natural product UK-2A (5.8 mmol, 3.0 g) in toluene (60 mL). The mixture was stirred an additional 15 min and quenched with EtOAc (20 mL). Hydrochloric acid (2N, 100 mL) was added slowly and stirred vigorously for 15 min. The layers were separated and the organic layer dried (MgSO4) and concentrated in vacuo to give 1.82 g (70%) of Compound 1 as a foamy, light yellow solid. Exact Mass: m/z calcd. for C22H24N2O8 [M]+=44.1533, found 444.1513. 1H-NMR data was consistent for Compound 1.

Aufarbeitung

  1. customquenched with EtOAc (20 mL)
  2. additionHydrochloric acid (2N, 100 mL) was added slowly
  3. stirringstirred vigorously for 15 min
  4. customThe layers were separated
  5. dry with materialthe organic layer dried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-094d4f47993d4ffcb9c12940b358c847
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903219B2

Notizen zur Reaktion

Wird geladen…