Sodium Chloride → HCID 70579374, Verbindung

HRID 1974178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1974178
[O:1]=[C:2]1[NH:5][C@@H:4]([C:6](OC)=[O:7])[C@H:3]1[NH:10][C:11](=[O:20])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+].[H][H].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>O1CCCC1.O.C(O)(=O)C>[OH:7][CH2:6][C@H:4]1[C@@H:3]([NH:10][C:11](=[O:20])[CH2:12][O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2](=[O:1])[NH:5]1

Komponenten

9

Edukt 5

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 53649703Methyl cis-3-phenoxyacetamido-4-oxoazetidine-2-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 70579374HCID 70579374, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 13.5 g (0.049 mole) of methyl cis-4-oxo-3-phenoxyacetylaminoazetidine-2-carboxylate in 975 ml of tetrahydrofuran and 100 ml of water at 0° (ice bath) was added a cold solution of 3.75 g (0.099 mole) of sodium borohydride in 250 ml of water over a period of 10 min. The solution was stirred at 0° for 40 min and then glacial acetic acid was added dropwise until hydrogen evolution ceased. Solid sodium bicarbonate and sodium chloride were added and this mixture was extracted five times with 250 ml portions of ethyl acetate. After drying the combined extracts (MgSO4), the solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate, clarified with Norite and allowed to crystallize to give the title compound; tlc: ethyl acetate, silica gel GF, Rf = 0.10; mp 153°-154 ° (ethyl acetate).

Aufarbeitung

  1. extractionthis mixture was extracted five times with 250 ml portions of ethyl acetate
  2. dry with materialAfter drying the combined extracts (MgSO4)
  3. customthe solvent was removed in vacuo
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. customto crystallize

Quellen und Nachweise

ORD-Eintrag
ord-e83b0dca19de4054af2de94d87a7d775
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US04000154

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