Hydrochloric Acid → 2-Phenylacetylamino-3,3-bis(4-fluorophenyl)propanoic acid

HRID 32870Notes

Reaction equation

HRID 32870 reaction equation
Cl.[NH2:2][CH:3]([CH:7]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5].[OH-].[Na+].[C:24]1([CH2:30][C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>C(OCC)(=O)C>[C:24]1([CH2:30][C:31]([NH:2][CH:3]([CH:7]([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[C:4]([OH:6])=[O:5])=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 14798Sodium Hydroxide2×HCID 159809952-Amino-3,3-bis(4-fluorophenyl)propanoic acid hydrochloride

Product 1

HCID 119778282-Phenylacetylamino-3,3-bis(4-fluorophenyl)propanoic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An aqueous solution (188 mL) of 2-amino-3,3-bis(4-fluorophenyl)propanoic acid hydrochloride (21.50 g, 68.9 mmol) was adjusted to pH 12.2 with 1M aqueous sodium hydroxide solution (154.2 g). Phenylacetyl chloride (10.8 mL, 81.7 mmol) was added dropwise at 0-10° C. while adjusting the mixture to pH 11-12 with 1M aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 3 hrs. Ethyl acetate (400 mL) was added to the reaction mixture, and the mixture was adjusted to pH 1.1 with concentrated hydrochloric acid and partitioned. The obtained organic layer was warmed to 40° C. and hexane (525 mL) was added. The mixture was cooled in an ice bath to allow solid precipitation. The solid was collected by filtration and dried to give the title compound (21.75 g).

Workup

  1. custompartitioned
  2. temperatureThe obtained organic layer was warmed to 40° C.
  3. additionhexane (525 mL) was added
  4. temperatureThe mixture was cooled in an ice bath
  5. customsolid precipitation
  6. filtrationThe solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-aea68b5a99f640e380dba9782256cca7
Source dataset
uspto-grants-2008_09
Patent number
US07427688B2

Reaction notes

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