Triethylamine → (3S,4S)-3-(tert-butoxycarbonylamino)-4-carbamoyloxymethyl-1-(p-nitrobenzyloxycarbonylmethoxy)-2-azetidinone

HRID 414857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414857
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@@H:12]([CH2:13][O:14][C:15](=[O:17])[NH2:16])[N:11]([OH:18])[C:10]1=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Br[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:30]>C(#N)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@@H:12]([CH2:13][O:14][C:15](=[O:17])[NH2:16])[N:11]([O:18][CH2:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C:10]1=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 70153214-Nitrobenzyl bromoacetateHCID 13489002(3S,4S)-3-(tert-butoxycarbonyl-amino)-4-carbamoyloxymethyl-1-hydroxy-2-azetidinone

Produkt 1

HCID 13489023(3S,4S)-3-(tert-butoxycarbonylamino)-4-carbamoyloxymethyl-1-(p-nitrobenzyloxycarbonylmethoxy)-2-azetidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In 40 ml of acetonitrile is dissolved 650 mg of (3S,4S)3-(tert-butoxycarbonylamino)-4-carbamoyloxymethyl-1-hydroxy-2-azetidinone, and 0.39 ml of triethylamine and 712 mg of p-nitrobenzyl bromoacetate are added to the solution under ice-cooling with stirring. The reaction solution is stirred at room temperature (15°-25° C.) for 3.5 hours. The solvent is distilled off under reduced pressure, and 50 ml of a mixed solution (1:1) of ethyl acetate and tetrahydrofuran and 50 ml of water are added to the residue. The organic layer is separated, washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The remaining crystals are treated with 15 ml of a mixed solution (1:2) of ether and hexane and filtered to give 98 mg (88.6%) of the above-identified comoound as crystals, m.p. 189°-191° C.

Aufarbeitung

  1. additionare added to the solution under ice-
  2. temperaturecooling
  3. stirringThe reaction solution is stirred at room temperature (15°-25° C.) for 3.5 hours
  4. distillationThe solvent is distilled off under reduced pressure, and 50 ml of a mixed solution (1:1) of ethyl acetate and tetrahydrofuran and 50 ml of water
  5. additionare added to the residue
  6. customThe organic layer is separated
  7. washwashed with aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionThe remaining crystals are treated with 15 ml of a mixed solution (1:2) of ether and hexane
  11. filtrationfiltered
  12. customto give 98 mg (88.6%) of the above-identified comoound as crystals, m.p. 189°-191° C.

Quellen und Nachweise

ORD-Eintrag
ord-b5e3d52483b3431c931ab63c0a0d7f6b
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04794108

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