Sulfuric Acid → (1RS,2RS,6RS)-9-Oxo-8-azabicyclo[4.3.0]non-4-ene-2-carboxylic acid

HRID 850717Notes

Reaction equation

HRID 850717 reaction equation
[O:1]=[C:2]1[CH:10]2[CH:5]([CH:6]=[CH:7][CH2:8][CH:9]2[C:11]([O:13]CC)=[O:12])[CH2:4][NH:3]1.S(=O)(=O)(O)O>O>[O:1]=[C:2]1[CH:10]2[CH:5]([CH:6]=[CH:7][CH2:8][CH:9]2[C:11]([OH:13])=[O:12])[CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 54398625ethyl (1RS,2RS,6RS)-9-oxo-8-azabicyclo[4.3.0]non-4-ene-2-carboxylate2×

Product 1

HCID 19365003(1RS,2RS,6RS)-9-Oxo-8-azabicyclo[4.3.0]non-4-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.36 g (40 nmol) of ethyl (1RS,2RS,6RS)-9-oxo-8-azabicyclo[4.3.0]non-4-ene-2-carboxylate (product A from Example K.2.) are stirred at 60° C. for 40 h with 30 ml of water and 5 g of conc. sulphuric acid. On cooling, the product precipitates. The precipitate is washed with a little cold water and dried in a vacuum drying oven at 50° C.

Workup

  1. temperatureOn cooling
  2. customthe product precipitates
  3. washThe precipitate is washed with a little cold water
  4. customdried in a vacuum
  5. customdrying oven at 50° C.

Sources & evidence

ORD record
ord-e3a307a405d144cea023aae95512431b
Source dataset
uspto-grants-2000_01
Patent number
US06018054

Reaction notes

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