Hydrochloric Acid → HCID 10088282, compound

HRID 1155557Notes

Reaction equation

HRID 1155557 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 m 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 adjusted to a pH of 2 with 1 N 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-a1b75b3ba53349f89caee2aef24c58d4
Source dataset
uspto-grants-1981_11
Patent number
US04302541

Reaction notes

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