Water → Benzyl (2-oxoazetidin-3-yl)carbamate

HRID 653180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653180
O[N:2]1[CH2:5][CH:4]([NH:6][C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C:3]1=[O:17].O.[OH-].[Na+]>O1CCCC1.[Cl-].[Cl-].[Cl-].[Ti+3]>[C:7]([NH:6][CH:4]1[CH2:5][NH:2][C:3]1=[O:17])([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Komponenten

6

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13036852HCID 13036852, Verbindung

Produkt 1

HCID 12834623Benzyl (2-oxoazetidin-3-yl)carbamateAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10313229titanium(III) trichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 118 mg (0.5 mmole) of N-hydroxy-3-(Cbz-amino)-2-azetidinone, prepared as described by Example 3, in 10 ml of tetrahydrofuran and 10 ml of water at pH 7 was added to a flask equipped with a magnetic stirrer, a buret, and a pH electrode. The solution was maintained under nitrogen and was treated with a solution of 0.8 ml of 20% titanium trichloride by dropwise addition from a syringe. The pH of the reaction mixture was maintained at 7.0 during the addition of the TiCl3 by the addition of 3.0N sodium hydroxide through the buret as needed. After the addition was complete the reaction mixture was stirred at room temperature for 2 hours. The pH of the reaction mixture was adjusted to 8.0, transferred to a separatory funnel and extracted with three 25 ml portions of ethyl acetate. The combined ethyl acetate was washed with 10 ml of brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was recrystallized from ethyl acetate-hexanes to give 69 mg (60%) of 3-(Cbz-amino)-2-azetidinone as a white solid melting at about 160° C. to about 161° C.

Aufarbeitung

  1. customequipped with a magnetic stirrer
  2. temperatureThe solution was maintained under nitrogen
  3. additionAfter the addition
  4. customtransferred to a separatory funnel
  5. extractionextracted with three 25 ml portions of ethyl acetate
  6. washThe combined ethyl acetate was washed with 10 ml of brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was recrystallized from ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-fbcf4ae56eca41b2a5675248a26f978a
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675399

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