3-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → HCID 86736468, compound

HRID 26320

Reaction equation

HRID 26320 reaction equation
[S:1]([CH:5]([N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[C:6](Cl)=[O:7])([OH:4])(=[O:3])=[O:2].[C:14]([O:17][CH2:18][C:19]1[CH2:26][S:25][CH:24]2[N:21]([C:22](=[O:28])[CH:23]2[NH2:27])[C:20]=1[C:29]([OH:31])=[O:30])(=[O:16])[CH3:15].C(=O)(O)[O-].[Na+]>CCOCC.O>[C:14]([O:17][CH2:18][C:19]1[CH2:26][S:25][CH:24]2[N:21]([C:22](=[O:28])[CH:23]2[NH:27][C:6](=[O:7])[CH:5]([S:1]([OH:4])(=[O:3])=[O:2])[N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)[C:20]=1[C:29]([OH:31])=[O:30])(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 867364672-Sulfo-2-(1-pyrryl)acetyl chloride

Product 1

HCID 86736468HCID 86736468, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-sulfo-2-(1-pyrryl)acetyl chloride (1 equivalent) in ether is added to 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid (1 equivalent) and sodium bicarbonate (about 3 equivalents) in water at about 0° C. After about 30 minutes the phases are separated, the pH adjusted to about 6.5 and the aqueous phase extracted with ethyl acetate. The ethyl acetate is dried over megnesium sulfate, filtered and evaporated to give the title compound.

Workup

  1. customAfter about 30 minutes the phases are separated
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. dry with materialThe ethyl acetate is dried over megnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-dad01d312966486fa7e7e8963f0579b3
Source dataset
uspto-grants-1979_04
Patent number
US04148998

Linked notes

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