Phenylacetyl chloride → 3-(4-Chlorophenyl)-3-(2-phenylacetamido)propanoic acid

HRID 850016Notes

Reaction equation

HRID 850016 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[C:16]1([CH2:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCOCC1>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([CH:2]([NH:1][C:23](=[O:24])[CH2:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][C:4]([OH:6])=[O:5])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 14798Sodium HydroxideHCID 3441763-Amino-3-(4-chlorophenyl)propanoic acid

Product 1

HCID 36831863-(4-Chlorophenyl)-3-(2-phenylacetamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9.6 g of 3-amino-3-(4-chlorophenyl)propionic acid are dissolved in 200 ml of dioxane and about 50 ml of 1N NaOH in order to reach pH=10.5-11.5. The medium is cooled to +5° C. and 6.34 ml of phenylacetyl chloride are then gradually added, while maintaining the mixture at pH=10.5-11.5 and at a temperature of between +5° C. and +10° C. Stirring is continued for 1 and a half hours and the medium is then concentrated to one-half before diluting with 500 ml of water. The resulting mixture is washed twice with EtOAc and then acidified to pH=1-2 by addition of 6N HCl. The solid is drained, washed with water and dried to give 14 g of the expected compound.

Workup

  1. temperatureThe medium is cooled to +5° C.
  2. temperaturewhile maintaining the mixture at pH=10.5-11.5
  3. customat a temperature of between +5° C. and +10° C
  4. customis continued for 1 and a half hours
  5. concentrationthe medium is then concentrated to one-half
  6. additionbefore diluting with 500 ml of water
  7. washThe resulting mixture is washed twice with EtOAc
  8. additionacidified to pH=1-2 by addition of 6N HCl
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-363a72cfaf944259a02eac6b5dd5756e
Source dataset
uspto-grants-2000_01
Patent number
US06015812

Reaction notes

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