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

HRID 558062Notes

Reaction equation

HRID 558062 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

1-Methylthiocarbonyloxyethyl benzoate (2g) (50 g), prepared as described in Gallop et al., U.S. Pat. No. 7,227,028, and lipase from Candida rugosa (2.5 g) were stirred in phosphate buffered saline, pH 7.2, (0.5 L) at room temperature. The progress of the reaction was monitored by 1H-NMR using the chiral solvating agent [(R)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol] and was complete within 16 h. The reaction mixture was diluted with ether and the ether layer separated and filtered through a pad of CELITE® to remove the enzyme. The ether phase was washed repeatedly with aqueous sodium bicarbonate then brine, and dried over anhydrous sodium sulfate (Na2SO4). Removing the solvent in vacuo afforded 22 g of the title compound (5) as a single enantiomer. 1H NMR (CDCl3, 400 MHz): 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. customat room temperature
  2. customthe ether layer separated
  3. filtrationfiltered through a pad of CELITE®
  4. customto remove the enzyme
  5. washThe ether phase was washed repeatedly with aqueous sodium bicarbonate
  6. dry with materialbrine, and dried over anhydrous sodium sulfate (Na2SO4)
  7. customRemoving the solvent in vacuo

Sources & evidence

ORD record
ord-89109a4b98cc4e7e8f04f20bfc7bbbf9
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

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