Acetic Anhydride → Acetoacetic Acid

HRID 4987

Reaktionsgleichung

Reaktionsgleichung von HRID 4987
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].C[C@H]1[C@@H](C(C)C)OC(=O)C2N(CCC=2)C(=O)C2=COC(=N2)CC(=O)C[C@H](O)C=C(C)C=CCN[C:12](=[O:13])[CH:11]=C1>N1C=CC=CC=1>[CH3:2][C:1]([O-:4])=[O:3].[CH3:11][C:12]([CH2:6][C:5]([OH:4])=[O:7])=[O:13]

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 5459319Virginiamycin M1

Produkt 2

HCID 96Acetoacetic AcidHCID 175Acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Acetic anhydride (45 ml) was added to a stirring solution of Virginiamycin M1 (6.5 g) in anhydrous pyridine (45 ml) at room temperature. After 30 minutes, ice-cold methanol (85 ml) was added in portions. Stirring was continued for 20 more minutes followed by flash evaporation to dryness at room temperature. The residue was partitioned between dichloromethane (3×300 ml) and saturated NaCl (aq, 300 ml). The organic layers were pooled, dried over anhydrous Na2SO4, flash evaporated to dryness (dry weight=8.1 g) and purified over E. Merck silica gel 60 column in hexane/acetone mixtures to give 1.0 g of the monoacetate and 1.58 g of the diacetate.

Aufarbeitung

  1. customfollowed by flash evaporation to dryness at room temperature
  2. customThe residue was partitioned between dichloromethane (3×300 ml) and saturated NaCl (aq, 300 ml)
  3. dry with materialdried over anhydrous Na2SO4, flash
  4. customevaporated to dryness (dry weight=8.1 g)
  5. custompurified over E

Quellen und Nachweise

ORD-Eintrag
ord-acac8f88fae84d0d92a648b8d5b90be2
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242938

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