3-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → HCID 86736110, compound

HRID 1448576Notes

Reaction equation

HRID 1448576 reaction equation
[S:1]([CH:5]([N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]=[O:15])[C:6](Cl)=[O:7])([OH:4])(=[O:3])=[O:2].[C:16]([O:19][CH2:20][C:21]1[CH2:28][S:27][CH:26]2[N:23]([C:24](=[O:30])[CH:25]2[NH2:29])[C:22]=1[C:31]([OH:33])=[O:32])(=[O:18])[CH3:17].C(=O)(O)[O-].[Na+]>CCOCC.O>[C:16]([O:19][CH2:20][C:21]1[CH2:28][S:27][CH:26]2[N:23]([C:24](=[O:30])[CH:25]2[NH:29][C:6](=[O:7])[CH:5]([S:1]([OH:4])(=[O:3])=[O:2])[N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[CH:14]=[O:15])[C:22]=1[C:31]([OH:33])=[O:32])(=[O:18])[CH3:17]

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 86736111HCID 86736111, compound

Product 1

HCID 86736110HCID 86736110, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-sulfo-2-(2-formyl-1-pyrryl)acetyl chloride (0.01 m) 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 (0.01 m) and sodium bicarbonate (0.03 m) in water. After 30 minutes the phases are separated, the pH adjusted to about 6.5 and the aqueous extracted with ethyl acetate. The ethyl acetate is separated from the aqueous phase, dried over magnesium sulfate and flash evaporated to give the title compound.

Workup

  1. customAfter 30 minutes the phases are separated
  2. extractionthe aqueous extracted with ethyl acetate
  3. customThe ethyl acetate is separated from the aqueous phase
  4. dry with materialdried over magnesium sulfate and flash
  5. customevaporated

Sources & evidence

ORD record
ord-a9bd1af5d8954b4d80904be67f6b7520
Source dataset
uspto-grants-1979_12
Patent number
US04180660

Reaction notes

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