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

HRID 653312Notes

Reaction equation

HRID 653312 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-31f5e320ad1b4c4f976cd1a69f3066a9
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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