Ethyl Acetate → 2-[(4R)-4-Acetylthio-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester

HRID 1065837

Reaktionsgleichung

Reaktionsgleichung von HRID 1065837
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][O:9][C:10](=[O:16])[CH:11]([O:13]CC)O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:19]([S:22][C@H:23]1[NH:26][C:25](=[O:27])[C@@H:24]1OC)(=[O:21])[CH3:20].C(OCC)(=O)C>C1(C)C=CC=CC=1.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10](=[O:16])[CH:11]([N:26]2[C@H:23]([S:22][C:19](=[O:21])[CH3:20])[CH2:24][C:25]2=[O:27])[OH:13])=[CH:17][CH:18]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 110433162-Ethoxy-2-hydroxyacetic acid p-nitrobenzyl esterHCID 56630779(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine

Produkt 1

HCID 538127912-[(4R)-4-Acetylthio-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

200 mg of 2-ethoxy-2-hydroxyacetic acid p-nitrobenzyl ester and 2 g of molecular sieves A4 are added to a solution of 54.5 mg of (3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine in a mixture of 4 ml of toluene and 1 ml of dimethylformamide, and the mixture is stirred for 2 hours at 50°. The molecular sieves are filtered off and the filtrate is concentrated in vacuo. The residue is chromatographed over silica gel, and by elution with toluene/ethyl acetate (9:1) the title compound, contaminated with some glyoxylate, is obtained. TLC: Rf =0.48 (ethyl acetate); IR spectrum (in CH2Cl2): absorption bands at 2.89 (broad), 5.64, 5.73, 5.91, 6.24, 6.56, 7.44, 7.62, 7.83-8.15 (broad, sh), 8.26, 8.39 and 8.80-9.30 (broad) μ.

Aufarbeitung

  1. filtrationThe molecular sieves are filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is chromatographed over silica gel
  4. washby elution with toluene/ethyl acetate (9:1) the title compound
  5. customis obtained
  6. customIR spectrum (in CH2Cl2): absorption bands at 2.89 (broad), 5.64, 5.73, 5.91, 6.24, 6.56, 7.44, 7.62, 7.83-8.15 (broad, sh), 8.26, 8.39 and 8.80-9.30 (broad) μ

Quellen und Nachweise

ORD-Eintrag
ord-f78a2e43378e4739a038ab95f5539bee
Quelldatensatz
uspto-grants-1982_05
Patentnummer
US04331676

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