Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → Methyl (2S)-2-[(4-bromophenyl)(4-fluorophenyl)methoxy]-4-methylpentanoate

HRID 1180408Notes

Reaction equation

HRID 1180408 reaction equation
ClC(Cl)(Cl)C(=N)O[CH:5]([C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH3:23][O:24][C:25](=[O:32])[C@H:26]([CH2:28][CH:29]([CH3:31])[CH3:30])[OH:27].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(Cl)Cl.C([O-])(O)=O.[Na+].CCOCC>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([CH:5]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)[O:27][C@@H:26]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]([O:24][CH3:23])=[O:32])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 9989388Methyl (2S)-2-hydroxy-4-methylpentanoateHCID 69472473(4-Bromophenyl)(4-fluorophenyl)methyl 2,2,2-trichloroethanimidoate

Product 1

HCID 86605383Methyl (2S)-2-[(4-bromophenyl)(4-fluorophenyl)methoxy]-4-methylpentanoate

Reagents, catalysts & solvents 3

HCID 516892Sodium BicarbonateCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the (4-bromophenyl)(4-fluorophenyl)methyl 2,2,2-trichloroethanimidoate of step 2 (1.18 mmol, 500 mg) in CH2Cl2 (5 mL) was added L-leucic acid methyl ester 2 (1.18 mmol, 146 mg) and then camphor sulfonic acid (0.12 mmol, 27 mg). The mixture was stirred at r.t. for 18 h. A few drops of saturated NaHCO3 was added, The mixture was diluted with ether and filtered. The filtrate was concentrated under reduced pressure and the crude product was chromatographed to give the title compound.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe crude product was chromatographed

Sources & evidence

ORD record
ord-7e0ae0b52a3745daa262016d1d34d347
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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