Triethylamine → Methyl cis-1-(2,4-dimethoxybenzyl)-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine-2-carboxylate

HRID 2050395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2050395
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9].C(N(CC)CC)C.[C:25]1([C:31]2[N:32]([CH2:43][C:44](Cl)=[O:45])[C:33](=[O:42])[O:34][C:35]=2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]1[C:44](=[O:45])[C@H:43]([N:32]2[C:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:34][C:33]2=[O:42])[C@@H:7]1[C:8]([O:10][CH3:11])=[O:9]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 106389553(2H)-Oxazoleacetyl chloride, 2-oxo-4,5-diphenyl-HCID 23470137Methyl (2E)-{[(2,4-dimethoxyphenyl)methyl]imino}acetate

Produkt 1

HCID 70576596Methyl cis-1-(2,4-dimethoxybenzyl)-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methyl N-(2,4-dimethoxybenzyl)iminoacetate (1.43 g) is dissolved in 13 ml of dry methylene chloride and 1 ml of triethylamine and cooled in an ice bath. A solution of 4,5-diphenyl-2-oxo-4-oxazolin-3-ylacetic acid chloride (2.0 g, 6.4 mmole) in 10 ml of methylene chloride is added over a 10 minute period. After one hour, the mixture is washed with water and 5% aqueous sodium bicarbonate then dried and evaporated to give a red oil which is chromatographed on silica gel to give methyl cis-1-(2,4-dimethoxybenzyl)-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine-2-carboxylate.

Aufarbeitung

  1. washthe mixture is washed with water and 5% aqueous sodium bicarbonate
  2. customthen dried
  3. customevaporated
  4. customto give a red oil which
  5. customis chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6f659a1df4b9459bb6f7af903b6bd80e
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04200572

Notizen zur Reaktion

Wird geladen…