HCID 58349494, compound → HCID 58560980, compound

HRID 2408161Notes

Reaction equation

HRID 2408161 reaction equation
C([O:5][C:6](=O)[CH:7]([CH:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)[CH2:16][CH2:17][CH3:18])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(C)(C)C>C1COCC1>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]([CH:15]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=2)[CH2:16][CH2:17][CH3:18])[CH2:6][OH:5])=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 58349494HCID 58349494, compound

Product 1

HCID 58560980HCID 58560980, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-chlorophenyl)-3-[4-(methoxycarbonyl)phenyl]hexanoic acid (prepared as described in PCT Patent Publication WO 2008/042223 A1 published on 10 Apr. 2008, 360 mg, 1.0 mmol) in anhydrous THF (10 mL) was cooled to 0° C., then borane dimethyl sulfide complex (0.3 mL, 3 mmol) was added slowly. The mixture was stirred at room temperature for five hours, then excess reagent was quenched with MeOH (2 mL). The mixture was concentrated, then the resulting residue was diluted with EtOAc (20 mL) and K2CO3 (aq). The organic layer was washed with water, dried over anhydrous Na2SO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 10% MeOH/DCM to afford the title compound. MS (M±H)+ 347.

Workup

  1. additionborane dimethyl sulfide complex (0.3 mL, 3 mmol) was added slowly
  2. customexcess reagent was quenched with MeOH (2 mL)
  3. concentrationThe mixture was concentrated
  4. additionthe resulting residue was diluted with EtOAc (20 mL) and K2CO3 (aq)
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-7c06dec85241460fbd6f6c54e9f45631
Source dataset
uspto-grants-2014_08
Patent number
US08809579B2

Reaction notes

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