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Hydrochloric Acid → (S)-Suprofen

HRID 1081555
Notes
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Reaction equation

HRID 1081555 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([CH3:18])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[O:12])=[CH:7][CH:6]=1.Cl>P([O-])([O-])([O-])=O>[CH3:1][O:2][C:3](=[O:19])[C@H:4]([CH3:18])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[O:12])=[CH:9][CH:10]=1.[CH3:18][C@@H:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[O:12])=[CH:7][CH:6]=1)[C:3]([OH:19])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3642305HCID 3642305, compound

Product 2

HCID 688580(S)-SuprofenHCID 11000255HCID 11000255, compound

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
22 °C

Procedure

To 100 mg crude Candida cylindracea lipase (Sigma L1754 Type VII, 500 units/mg solid) in 4 mL 0.2 M phosphate buffer, pH 7.0, was added 200 mg (±)-α-methyl-4-(2-thienylcarbonyl)benzeneacetic acid methyl ester (suprofen methyl ester). The resulting suspension was gently stirred with a magnetic stirrer for 48 hours at 22° C. The reaction mixture was acidified to pH 1.0 with 1 N HCl and exhaustively extracted with ethyl acetate three times. The combined organic extract was dried over sodium sulfate and was then evaporated to dryness. The residue was chromatographed over a silica gel (MN Kieselgel 60) column (0.8×15 cm). Elution of the column with a solvent system consisting of ethyl acetate-hexane (1:5) gave unreacted (R)-α-methyl-4-(2-thienylcarbonyl)benzeneacetic acid methyl ester, [α]D25 =-54.7° (c=3.9, CHCl3), ee>0.90, and (S)-α-methyl-4-(2-thienylcarbonyl)benzeneacetic acid, [α]D25 =+43.5° (c=2.1, CHCl3), ee>0.95. The optical purity expressed as enantiomeric excess (ee) is determined by proton magnetic resonance spectroscopy of the methyl ester in the presence of the chiral lanthanide shift reagent, Eu(hfc)3.

Workup

  1. extractionexhaustively extracted with ethyl acetate three times
  2. extractionThe combined organic extract
  3. dry with materialwas dried over sodium sulfate
  4. customwas then evaporated to dryness
  5. customThe residue was chromatographed over a silica gel (MN Kieselgel 60) column (0.8×15 cm)
  6. washElution of the column with a solvent system

Sources & evidence

ORD record
ord-37117e28aa564e36b232f185bd7f5c3e
Source dataset
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05587318

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes