6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid → HCID 22748504, compound

HRID 1390224Notes

Reaction equation

HRID 1390224 reaction equation
C(OS([CH:7]([C:11]1[CH:12]=[CH:13][C:14]2[O:18][CH2:17][CH2:16][C:15]=2[CH:19]=1)[C:8]([OH:10])=O)(=O)=O)C.[S:20](Cl)(Cl)=[O:21].O.[NH2:25][CH:26]1[C:32](=[O:33])[N:31]2[CH:27]1[S:28][C:29]([CH3:38])([CH3:37])[CH:30]2[C:34]([OH:36])=[O:35].C(=O)(O)[O-:40].[Na+].[CH3:44][CH2:45][O:46]CC>C(OCC)(=O)C>[CH2:45]([O:46][S:20]([CH:17]1[CH2:16][C:15]2[CH:19]=[C:11]([CH2:7][C:8]([NH:25][CH:26]3[C:32](=[O:33])[N:31]4[CH:27]3[S:28][C:29]([CH3:38])([CH3:37])[CH:30]4[C:34]([OH:36])=[O:35])=[O:10])[CH:12]=[CH:13][C:14]=2[O:18]1)(=[O:21])=[O:40])[CH3:44]

Participants

8

Reactant 6

HCID 1626-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidHCID 962WaterHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 23335847HCID 23335847, compound2×

Product 1

HCID 22748504HCID 22748504, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethoxysulfonyl(2,3-dihydro-5-benzofuranyl)acetic acid (5 mmole) in 50 ml of dry ether is reacted with about 5.5 mmole 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. It is then redissolved in 10 ml of ether. This ether solution is added to 10 ml of water containing 5 mmole of 6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-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. dissolutionIt 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-a82fbbc229a04e62909efcc91572dc3d
Source dataset
uspto-grants-1979_02
Patent number
US04138397

Reaction notes

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