Sodium Iodide → HCID 10282284, Verbindung

HRID 895794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895794
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].[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:43]([CH:45]([CH3:47])[CH3:46])=[O:44].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C(Cl)Cl>[CH3:46][CH:45]([CH3:47])[C:43]([O:42][C@@H:13]1[C@@H:14]([CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:15](=[O:16])[O:17][CH2:18][C@H:19]([NH:23][C:24]([C:26]2[C:31]([O:32][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)=[O:25])[C:20](=[O:21])[O:22][C@H:12]1[CH3:11])=[O:44]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 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-methylpropanoate

Produkt 1

HCID 10282284HCID 10282284, VerbindungAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzyl bromide (0.233 mol, 27.7 mL) was added to a solution of NaI (0.097 mol, 14.5 g) in acetone (1 L). Natural product UK-2A (1) (0.194 mol, 100 g) was added followed by powdered K2CO3 (0.388 mol, 53 g) and the mixture stirred vigorously overnight. The mixture was diluted with CH2Cl2 (500 mL) and washed with H2O (2×500 mL). The organic layer was dried (MgSO4), and concentrated in vacuo. Recrystallization (EtOAc/hexane) gave 95.5 g (79%) of 2 as an off-white solid (m.p. 169-170° C.) which contained ˜6.5% N-benzylated product (LC-MS). 1H-NMR and MS (M+1 605) were consistent for the title compound (2). The compound was used in the next step without further purification. The N-benzylated by-product could be removed from the mixture prior to recrystallization by filtration of the crude reside through a plug of silica gel (30% acetone/hexane as the eluent).

Aufarbeitung

  1. washwashed with H2O (2×500 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customRecrystallization (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c8eb4abe5cf34cc28168619f147843dd
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916932B2

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