Hydrochloric Acid → HCID 10088282, compound

HRID 570030Notes

Reaction equation

HRID 570030 reaction equation
FC(F)(F)C([O-])=O.[NH2:8][C@H:9]1[C:16](=[O:17])[N:15]2[C@@H:10]1[CH2:11][CH2:12][C:13]([Cl:21])=[C:14]2[C:18]([OH:20])=[O:19].C(=O)(O)[O-].[Na+].[C:27]1([CH2:33][C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>O.CC(C)=O>[C:27]1([CH2:33][C:34]([NH:8][C@H:9]2[C:16](=[O:17])[N:15]3[C@@H:10]2[CH2:11][CH2:12][C:13]([Cl:21])=[C:14]3[C:18]([OH:20])=[O:19])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 84468TrifluoroacetateHCID 516892Sodium BicarbonateHCID 12878908HCID 12878908, compound

Product 1

HCID 10088282HCID 10088282, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

In this Example, 150 mg (0.45 m mole) of the trifluoroacetate of (±)-cis-7-amino-3-chloro-1-azabicyclo-[4,2,0]oct-2-en-8-on-2-carboxylic acid prepared as in the method described in JPUPA No. 87791/80 is dissolved in a mixture of 2 ml of water and 2 ml of acetone and 134 mg (1.5 m mole) of sodium bicarbonate is added to the solution to make the solution homogeneous. To the mixture is added 84.2 mg (0.54 mole) of phenylacetylchloride dissolved in 0.5 ml of acetone under cooling in one hour and the mixture is stirred for 3 hours. The reaction mixture is added to a pH of 2 with 1N hydrochloric acid and extracted 5 times with 2 ml of ethyl acetate. The extract is concentrated under reduced pressure and dried to obtain 80 mg (55.0%) of the desired compound.

Workup

  1. additionis added to the solution
  2. temperatureunder cooling in one hour
  3. extractionextracted 5 times with 2 ml of ethyl acetate
  4. concentrationThe extract is concentrated under reduced pressure
  5. customdried

Sources & evidence

ORD record
ord-cb8d544896d24656be5c49e05388fdfa
Source dataset
uspto-grants-1988_03
Patent number
US04734494

Reaction notes

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