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

HRID 2231594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2231594
[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-chloroacetamido-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-ce8fb2f19d194b628ad9a3b27ebdd511
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04782147

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