Phenylacetyl chloride → HCID 15449592, compound

HRID 1280389Notes

Reaction equation

HRID 1280389 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:10][C:11]([OH:13])=[O:12])[NH2:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:21]1([CH2:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.CC(C)=O>[C:21]1([CH2:27][C:28]([NH:9][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:10][C:11]([OH:13])=[O:12])=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 27641783-amino-3-(3-chlorophenyl)propanoic acid

Product 1

HCID 15449592HCID 15449592, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
-5 °C

Procedure

To a solution, in a 3/1 mixture of water/acetone, of 10 mmol of (±)-3-(3-chlorophenyl)-β-alanine described in Step A of Example 1 there are added 24 mmol of triethylamine and then, at −5° C., 13 mmol of phenylacetyl chloride. After stirring for 2 hours at −5° C. and then for 3 hours at ambient temperature, the solution is filtered; the acetone is evaporated off, the aqueous phase is washed with ether and is then acidified to pH=1 and extracted with ethyl acetate. The combined organic phases are dried and then evaporated. The residue obtained is washed with hexane, precipitated in a minimum of ether and then filtered to yield the expected product.

Workup

  1. customat −5° C.
  2. waitfor 3 hours at ambient temperature
  3. filtrationthe solution is filtered
  4. customthe acetone is evaporated off
  5. washthe aqueous phase is washed with ether
  6. extractionextracted with ethyl acetate
  7. customThe combined organic phases are dried
  8. customevaporated
  9. customThe residue obtained
  10. washis washed with hexane
  11. customprecipitated in a minimum of ether
  12. filtrationfiltered

Sources & evidence

ORD record
ord-01e397090fdb4e03972c6403e61720d7
Source dataset
uspto-grants-2002_09
Patent number
US06451789B1

Reaction notes

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