Carbamic acid 2,6-di-sec-butylphenyl ester → (r,r,r)-1-Phenylethylcarbamic acid-2,6-di-sec-butylphenyl ester

HRID 885789Notes

Reaction equation

HRID 885789 reaction equation
[CH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH2:13][CH3:14])[CH3:12])[C:6]=1[O:15][C:16](=[O:18])[NH2:17])([CH2:3][CH3:4])[CH3:2]>CCCCCC.C(OCC)(=O)C>[C@H:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C@@H:11]([CH2:13][CH3:14])[CH3:12])[C:6]=1[O:15][C:16](=[O:18])[NH:17][C@@H:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:2])([CH2:3][CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 66725334Carbamic acid 2,6-di-sec-butylphenyl ester

Product 1

HCID 66725105(r,r,r)-1-Phenylethylcarbamic acid-2,6-di-sec-butylphenyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To an Agilent HPLC system fitted with a diode array detector and a 0.46 cm ID×25 cm long 10 mm KROMASIL Silica Column was charged 714 mg of racemic R-(+)-1-phenyl-ethyl)-carbamic acid-2,6-di-sec-butylphenyl ester dissolved in 10 ml of hexane/ethyl acetate (98:2) to give a 71.4 g/l feed solution. The sample was eluted with hexane/ethyl acetate (98:2) at 2 ml/min at 25° C. Fractions containing (R,R,R)-1-phenylethylcarbamic acid-2,6-di-sec-butylphenyl ester were collected and evaporated under reduced pressure at <55° C. At the highest loading, the (R,R,R)-stereoisomer was collected with a chiral purity of 98.7% diastereomeric excess (de) and a total yield of 53%.

Workup

  1. customTo an Agilent HPLC system fitted with a diode array detector
  2. customto give a 71.4 g/l feed solution
  3. washThe sample was eluted with hexane/ethyl acetate (98:2) at 2 ml/min at 25° C
  4. additionFractions containing (R,R,R)-1-phenylethylcarbamic acid-2,6-di-sec-butylphenyl ester
  5. customwere collected
  6. customevaporated under reduced pressure at <55° C
  7. customAt the highest loading, the (R,R,R)-stereoisomer was collected with a chiral purity of 98.7% diastereomeric excess (de)

Sources & evidence

ORD record
ord-f1e048cec57c4e618c7b3bf0d929d229
Source dataset
uspto-grants-2012_08
Patent number
US08242315B2

Reaction notes

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