Hydrochloric Acid → HCID 10088282, compound

HRID 1156395Notes

Reaction equation

HRID 1156395 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>CC(C)=O.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 mmole) of trifluoroacetate of (±)-cis-7-amino-3-chloro-1-azabicyclo[4,2,0]oct-2-en-8-on-2-carboxylic acid is suspended in a mixed solvent of 2 ml of water and 2 ml of acetone, 134 mg (1.5 mmole) of sodium bicarbonate is added thereto to make a homogeneous solution. To the solution is added dropwise a solution of 84.2 mg (0.54 mmole) of phenylacetyl chloride in 0.5 ml of acetone under ice cooling in one hour. The mixture is stirred for 3 hours, adjusted to pH 2 with 1 N hydrochloric acid and extracted 5 times with each 2 ml of ethyl acetate. The extract is concentrated under reduced pressure and the residue is dried to obtain 80 mg (55.0%) of the desired compound.

Workup

  1. additionis added
  2. extractionextracted 5 times with each 2 ml of ethyl acetate
  3. concentrationThe extract is concentrated under reduced pressure
  4. customthe residue is dried

Sources & evidence

ORD record
ord-1c7392610c6746788255a0f725ed24b1
Source dataset
uspto-grants-1982_06
Patent number
US04335211

Reaction notes

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