(-)-2,2,2-Trifluoro-1-(9-anthryl)ethanol → (1r)-1-Methylthiocarbonyloxyethyl benzoate

HRID 558054Notes

Reaction equation

HRID 558054 reaction equation
C(O[CH2:10][CH2:11][O:12][C:13]([CH3:15])=[S:14])(=O)C1C=CC=CC=1.FC(F)(F)[C@@H:18]([C:20]1[C:21]2[C:26]([CH:27]=[C:28]3[C:33]=1C=CC=C3)=CC=CC=2)[OH:19].[OH:36]P([O-])(O)=O.OP([O-])([O-])=O.[Na+].[Na+].[Na+].[Cl-].[Cl-].[K+].[K+]>CCOCC>[C:18]([O:19][C@H:11]([O:12][C:13]([CH3:15])=[S:14])[CH3:10])(=[O:36])[C:20]1[CH:33]=[CH:28][CH:27]=[CH:26][CH:21]=1

Participants

5

Reactant 3

HCID 7006444(-)-2,2,2-Trifluoro-1-(9-anthryl)ethanolHCID 24978514Phosphate Buffered SalineHCID 87231740Methylthiocarbonyloxyethyl benzoate

Product 1

HCID 87231909(1r)-1-Methylthiocarbonyloxyethyl benzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-methylthiocarbonyloxyethyl benzoate (2g) (50 g) and lipase from Candida rugosa (2.50 g) in pH 7.2 phosphate buffered saline (500 mL) was stirred at room temperature. The reaction was monitored by 1H-NMR using the chiral solvating agent (R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol. The reaction was complete after ca. 12 hours. The reaction mixture was diluted with ether and the ether layer separated and filtered through a pad of CELITE® 545 to remove the enzyme. The ether layer was washed with aqueous sodium bicarbonate (NaHCO3) (5 times) and brine, and dried over anhydrous sodium sulfate (Na2SO4). After the solvent was removed by rotary evaporation, 22 g of the title compound (5) was obtained. 1H-NMR using a chiral solvating agent showed a single isomer and the absolute configuration was confirmed by derivatization to a compound having a known stereochemistry. 1H-NMR (CDCl3): δ 1.65 (d, J=5.6 Hz, 3H), 2.35 (s, 3H), 7.20 (q, J=5.6 Hz, 1H), 7.45 (m, 2H), 7.58 (m, 1H), 8.06 (m, 2H) ppm.

Workup

  1. customthe ether layer separated
  2. filtrationfiltered through a pad of CELITE® 545
  3. customto remove the enzyme
  4. washThe ether layer was washed with aqueous sodium bicarbonate (NaHCO3) (5 times) and brine
  5. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  6. customAfter the solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-8febd0b69c6a454f9fd66b79fef40240
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

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