Triethylamine → 4-nitrobenzyl 2-diazo-4-[(2R,3S)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

HRID 851421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851421
[CH3:1][C:2]([C@H:18]1[C:21](=[O:22])[NH:20][C@@H:19]1[CH2:23][C:24](=[O:39])[CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:27])([O:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:6])[CH3:3].C1(C)C=CC(S([N:49]=[N+:50]=[N-])(=O)=O)=CC=1.C(N(CC)CC)C>C(#N)C>[N+:49](=[C:25]([C:24](=[O:39])[CH2:23][C@@H:19]1[C@@H:18]([C:2]([CH3:1])([O:4][C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[O:6])[CH3:3])[C:21](=[O:22])[NH:20]1)[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=1)=[O:27])=[N-:50]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 867388734-nitrobenzyl 4-[(2R,3S)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

Produkt 1

HCID 867388744-nitrobenzyl 2-diazo-4-[(2R,3S)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoateAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-nitrobenzyl 4-{(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidine-2-yl}-3-oxobutanoate (58.3 mg) in acetonitrile (1.17 ml) was added a solution of p-toluenesulfonyl azide (25.3 mg) in acetonitrile (0.228 ml) at 0° C. After stirring for 5 minutes at 0° C., a solution of triethylamine (53.7 μl) in acetonitrile (0.483 ml) was added dropwise. The stirring mixture was allowed to warm to ambient temperature during 15 minutes and kept at the same temperature for 20 minutes. The solvent was distilled off and the residue (85.9 mg) was flash chromatographed on silica gel (1 g) eluting with a mixture of methylene chloride and ethyl acetate (50:1 to 3:1) to give 4-nitrobenzyl 2-diazo-4-{(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidine-2-yl}-3-oxobutanoate (58.4 mg) as an amorphous solid

Aufarbeitung

  1. temperatureto warm to ambient temperature during 15 minutes
  2. waitkept at the same temperature for 20 minutes
  3. distillationThe solvent was distilled off
  4. customchromatographed on silica gel (1 g)
  5. washeluting with a mixture of methylene chloride and ethyl acetate (50:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-c02bf8e040324a5fbabaf91cbb74f5e5
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04383945

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