Triethylamine → Benzyl 3-(alpha-azidoacetoxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1164337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1164337
[N:1]([CH2:4][C:5](Cl)=[O:6])=[N+:2]=[N-:3].C(N(CC)CC)C.[N:15]12[C:21](=[O:22])[CH2:20][CH:19]1[CH2:18][C:17](=[O:23])[CH:16]2[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[N:1]([CH2:4][C:5]([O:23][C:17]1[CH2:18][CH:19]2[N:15]([C:21](=[O:22])[CH2:20]2)[C:16]=1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:6])=[N+:2]=[N-:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 109095582-azidoacetyl ChlorideHCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Produkt 1

HCID 15136298Benzyl 3-(alpha-azidoacetoxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Azidoacetyl chloride (21 μl) is added by syringe in an ice-cold, stirring solution of triethylamine (42 μl) and benzyl 1-azabicyclo[3.2.0]heptane-3,7-dione-2-carboxylate (52 mg) in anhydrous methylene chloride (2 ml). After stirring 30 mins in the cold, the reaction mixture is diluted with methylene chloride (5 ml), washed with H2O (2 ml), pH 3 phosphate buffer (2 ml), and 5% NaHCO3 (2 ml), dried with MgSO4, filtered, and evaporated in vacuo. Chromatography of the residue on a silica gel GF plate gives benzyl 3-(α-azidoacetoxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Aufarbeitung

  1. washwashed with H2O (2 ml), pH 3 phosphate buffer (2 ml), and 5% NaHCO3 (2 ml)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a5f67516a9ca4799a8b53c26502b988c
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04369187

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