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Bromine → Sodium

HRID 372614
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 372614
[Na:1].[CH3:2][CH2:3][C@@H:4]([C:23]([C@H:25]([C@@H:27]([OH:43])[C@@H:28]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([OH:39])[C:33]=1[C:40]([OH:42])=[O:41])[CH3:29])[CH3:26])=[O:24])[C@H:5]1[O:9][C@@:8]([C@@H:12]2[O:17][C@@H:16]([CH3:18])[C@@:15]([OH:21])([CH2:19][CH3:20])[CH2:14][CH2:13]2)([CH2:10][CH3:11])[CH2:7][C@@H:6]1[CH3:22].[Br:44]Br>C(=S)=S>[Br:44][C:37]1[C:32]([CH2:31][CH2:30][CH:28]([CH3:29])[CH:27]([OH:43])[CH:25]([CH3:26])[C:23](=[O:24])[CH:4]([CH2:3][CH3:2])[CH:5]2[CH:6]([CH3:22])[CH2:7][C:8]([CH2:10][CH3:11])([CH:12]3[CH2:13][CH2:14][C:15]([CH2:19][CH3:20])([OH:21])[CH:16]([CH3:18])[O:17]3)[O:9]2)=[C:33]([C:40]([OH:42])=[O:41])[C:34]([OH:39])=[C:35]([CH3:38])[CH:36]=1.[Na:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24408BromineHCID 5360545SodiumHCID 5360807Lasalocid

Produkt 2

HCID 5360545SodiumHCID 23277601HCID 23277601, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon Disulfide
Lösungsmittel

Versuchsvorschrift

To a solution of 1.53 g of the sodium salt of antibiotic X-537A in 30 ml carbon disulfide was added dropwise a solution of 0.14 ml bromine 10 ml carbon disulfide at -5° over 10 minutes. The solvent was removed under a stream of nitrogen at room temperature (approximately 2 hours). The residue was purified by dissolving it in ethyl acetate and the solution washed successively with aqueous sodium bisulfite and sodium carbonate. After drying (Na2SO4), the solution was evaporated under reduced pressure and the residue crystallized from ethyl acetate to give 5-bromo-3-methyl-6{-7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydro-pyranyl)-2-tetrahydrofuryl]heptyl} salicylic acid, sodium salt as colorless cubes, m.p. 185°, [α]D25 -7.36° (1% in methanol).

Aufarbeitung

  1. customThe solvent was removed under a stream of nitrogen at room temperature (approximately 2 hours)
  2. customThe residue was purified
  3. dissolutionby dissolving it in ethyl acetate
  4. washthe solution washed successively with aqueous sodium bisulfite and sodium carbonate
  5. dry with materialAfter drying (Na2SO4)
  6. customthe solution was evaporated under reduced pressure
  7. customthe residue crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1dfa767a45e741c295835fa2761d32b8
Quelldatensatz
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE029651

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