2-Bromo-1,1-dimethoxyethane → HCID 86746812, Verbindung

HRID 248261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248261
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:54])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([N:50]=[N+:51]=[N-:52])[CH:46]([OH:53])[CH2:45]2)[CH:7]([CH3:55])[CH2:6][CH2:5][C:4]1=[O:56])[CH3:2].[H-].[K+].[CH3:59][O:60][CH:61]([O:64][CH3:65])[CH2:62]Br>>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:54])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([N:50]=[N+:51]=[N-:52])[CH:46]([O:53][CH2:62][CH:61]([O:64][CH3:65])[O:60][CH3:59])[CH2:45]2)[CH:7]([CH3:55])[CH2:6][CH2:5][C:4]1=[O:56])[CH3:2]

Komponenten

4

Edukt 3

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 82127Potassium hydrideHCID 8674680817-Ethyl-1-hydroxy-12-[2'-(4"-azido-3"-hydroxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

Produkt 1

HCID 86746812HCID 86746812, Verbindung

Versuchsvorschrift

Alternatively, a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-azido-3"-hydroxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (25 mg, Example 42, in 0.2 ml dry DME) is added to a stirring suspension of potassium hydride (1 equivalent in 0.5 ml DME) followed immediately by addition of a large excess of bromoacetaldehyde dimethyl acetal (0.2 ml). After 2 hours the mixture is quenched with saturated ammonium chloride and extracted with ethyl acetate. The combined organics are dried over magnesium sulfate and concentrated in vacuo. The product is purified by preparative tlc on silica gel to give the title compound.

Aufarbeitung

  1. customAfter 2 hours the mixture is quenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organics are dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe product is purified by preparative tlc on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-365ba665b9174e0b869877ff489595a0
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208228

Notizen zur Reaktion

Wird geladen…