Hydrochloric Acid → HCID 28285778, compound

HRID 1425920Notes

Reaction equation

HRID 1425920 reaction equation
[C:1]([NH:4][CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].Cl>[OH-].[Na+].O>[C:1]([NH:4][C@H:5]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 108499842-acetamido-3-[4-(trifluoromethyl)phenyl]propanoic Acid

Product 1

HCID 28285778HCID 28285778, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid (LXIII) (30 g, 109 mol) in 1 M NaOH (50 mL) and water (1 L) was adjusted to pH 7.6-7.8 before adding CoCl2 (300 mg, 2.3 mmol) and Acylase I (3 g) (from Aspergilus melleus). The reaction was stirred at room temperature under argon for 2 days at which time Marfey's test was performed and additional enzyme (1 g) was added and the reaction was stirred for an additional day. The mixture was acidified with 2 M HCl to pH 1 and extracted with EtOAc (3×) (the aqueous phase containing the L-enantiomer (LXIV) was saved). The combined organic extracts were washed with 2 M HCl (3×), brine (3×) and dried over MgSO4. The solvent was removed under reduced pressure and the residue was recrystallized from EtOAc/hexane, affording (R)-2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid (LXV) (10.2 g, 37 mmol, 68% yield).

Workup

  1. additionadditional enzyme (1 g) was added
  2. stirringthe reaction was stirred for an additional day
  3. extractionextracted with EtOAc (3×) (the aqueous phase
  4. additioncontaining the L-enantiomer (LXIV)
  5. washThe combined organic extracts were washed with 2 M HCl (3×), brine (3×)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-797c23a6bca04b1e9131e9229055a83c
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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