Sodium Bicarbonate → Methyl cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-allyloxyiminoacetamido]-2-oxoazetidine-4-carboxylate

HRID 978899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 978899
[NH2:1][C@H:2]1[C@@H:5]([C:6]([O:8][CH3:9])=[O:7])[NH:4][C:3]1=[O:10].C(=O)([O-])O.[Na+].Cl.[Cl:17][CH2:18][C:19]([NH:21][C:22]1[S:23][CH:24]=[C:25](/[C:27](=[N:31]/[O:32][CH2:33][CH:34]=[CH2:35])/[C:28](Cl)=[O:29])[N:26]=1)=[O:20]>O1CCCC1.O>[Cl:17][CH2:18][C:19]([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:31][O:32][CH2:33][CH:34]=[CH2:35])[C:28]([NH:1][C@H:2]2[C@@H:5]([C:6]([O:8][CH3:9])=[O:7])[NH:4][C:3]2=[O:10])=[O:29])[N:26]=1)=[O:20]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 21244940(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-prop-2-enoxyiminoacetyl chloride;hydrochlorideHCID 53988551cis-3-Amino-4-methoxycarbonyl-2-oxoazetidine

Produkt 1

HCID 86740476Methyl cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-allyloxyiminoacetamido]-2-oxoazetidine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a mixture of 2 ml of tetrahydrofuran and 2 ml of water is dissolved 185.5 mg of methyl cis-3-amino-2-oxoazetidine-4-carboxylate and under ice-cooling and stirring 469.6 mg of sodium hydrogen carbonate and successively, 600 mg of 2-(2-chloroacetamido-4-thiazolyl)-(Z)-allyloxyiminoacetyl chloride hydrochloride is added. The mixture is stirred at room temperature for 2 hours and concentrated under reduced pressure. To the residue is added 20 ml of water and the insolubles are collected by filtration, washed with aqueous sodium hydrogen carbonate, water, hexane and ether in this order, and dried to give methyl cis-3-[2-(2-chloracetamido-4-thiazolyl)-2-allyloxyiminoacetamido]-2-oxoazetidine-4-carboxylate (syn isomer) as light-yellow granules, m.p. 270°-280° C. (decomp.).

Aufarbeitung

  1. temperatureunder ice-cooling
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue is added 20 ml of water
  4. filtrationthe insolubles are collected by filtration
  5. washwashed with aqueous sodium hydrogen carbonate, water, hexane and ether in this order
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bb5ec5158a044f77bf54b1312c139b5f
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04665067

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