Water → HCID 23335851, compound

HRID 904029Notes

Reaction equation

HRID 904029 reaction equation
O1C2C=CC(CC(O)=O)=CC=2CC1.S(Cl)(Cl)=O.[CH2:18]([O:20][S:21]([CH:24]([C:28]1[CH:29]=[CH:30][C:31]2[O:35][CH2:34][CH2:33][C:32]=2[CH:36]=1)[C:25]([OH:27])=O)(=[O:23])=[O:22])[CH3:19].O.[NH2:38][CH:39]1[C:46](=[O:47])[N:45]2[CH:40]1[S:41][CH2:42][C:43]([CH3:51])=[C:44]2[C:48]([OH:50])=[O:49].C(=O)(O)[O-].[Na+]>CCOCC.C(OCC)(=O)C>[CH2:18]([O:20][S:21]([CH:24]([C:28]1[CH:29]=[CH:30][C:31]2[O:35][CH2:34][CH2:33][C:32]=2[CH:36]=1)[C:25]([NH:38][CH:39]1[C:46](=[O:47])[N:45]2[CH:40]1[S:41][CH2:42][C:43]([CH3:51])=[C:44]2[C:48]([OH:50])=[O:49])=[O:27])(=[O:22])=[O:23])[CH3:19]

Participants

9

Reactant 6

HCID 962WaterHCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 27374552,3-Dihydro-5-benzofuranacetic acidHCID 23335847HCID 23335847, compound

Product 1

HCID 23335851HCID 23335851, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

α-Ethoxysulfonyl(2,3-dihydro-5-benzofuranyl acetic acid (5mmole) in 50 ml of dry ether is reacted with about 5.5 mole of thionyl chloride at 20° C. for 4 hours. At the end of this time the solvent is removed to insure that all of the thionyl chloride and hydrochloric acid is removed. The residue is then redissolved in 10 ml of ether. This ether solution is added to 10 ml of water containing 5 mmole of 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and 10 mmole of sodium bicarbonate. The temperature of the aqueous solution is about 10° C. After stirring for about 2 hours, the pH is adjusted to about 2. Ethyl acetate is added, the mixture is thoroughly agitated and the layers separated. The organic layer is dried over magnesium sulfate, filtered and evaporated to give the title compound.

Workup

  1. customAt the end of this time the solvent is removed
  2. customis removed
  3. dissolutionThe residue is then redissolved in 10 ml of ether
  4. customis about 10° C
  5. stirringthe mixture is thoroughly agitated
  6. customthe layers separated
  7. dry with materialThe organic layer is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-023ae5bd5b6f42399f5eb6adbb3b79df
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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