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Water → 6,9-Diacetoxy-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carboxylic acid

HRID 236597
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 236597
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:31]=[O:32])[CH:8]=[C:9]2[C:17]=1[CH:16]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[C:15]1([O:24][C:25](=[O:27])[CH3:26])[O:23][N:10]2[CH2:11][CH:12]2[CH:14]1[N:13]2C(=O)C)(=[O:3])[CH3:2].O.S(=O)(=O)(O)[OH:35].C(O)(C)C>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:31]([OH:35])=[O:32])[CH:8]=[C:9]2[C:17]=1[CH:16]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[C:15]1([O:24][C:25](=[O:27])[CH3:26])[O:23][N:10]2[CH2:11][CH:12]2[CH:14]1[NH:13]2)(=[O:3])[CH3:2]
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Komponenten

7

Edukt 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 133974FR 66973

Produkt 1

HCID 150517396,9-Diacetoxy-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10219390
chromium (VI) trioxide
Katalysator
HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 11-acetyl-8-carbamoyloxymethyl-4-formyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (29 mg) in acetone (2 ml) was added a mixture of chromium trioxide (26 mg), water (76 μl) and sulfuric acid (22 μl) in an ice-water bath. After stirring for 30 minutes in an ice-water bath, isopropyl alcohol (2 ml) was added to the reaction mixture. The resultant mixture was then poured into water (10 ml) and extracted with a mixture of chloroform and methanol (2:1, v/v) (10 ml×5). The extracts were combined and dried over magnesium sulfate, and then evaporated in vacuo. The residue was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform, methanol and water (65:25:4, v/v) to afford 6,9-diacetoxy-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carboxylic acid (5 mg).

Aufarbeitung

  1. extractionextracted with a mixture of chloroform and methanol (2:1
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. additionwas developed with a mixture of chloroform, methanol and water (65:25:4, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-d9e86cd46b4140eea13d54ee2ac6972a
Quelldatensatz
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04645765

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