Sodium Hydroxide → HCID 11188926, compound

HRID 2306156Notes

Reaction equation

HRID 2306156 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:20])[CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:25]=1[CH2:26]Br>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:13]1[C:14]([CH3:20])=[CH:15][CH:16]=[CH:17][C:18]=1[CH3:19])[CH2:11][O:12][CH2:26][C:25]1[C:24]([F:23])=[CH:31][CH:30]=[CH:29][C:28]=1[F:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 11818312HCID 11818312, compound

Product 1

HCID 11188926HCID 11188926, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

19 g (68 mmol) of N-tert.-butoxycarbonyl-3-hydroxy-2-(2,6-dimethylphenyl)-propylamine are dissolved in 150 ml CH2Cl2, mixed with 100 ml of 50% sodium hydroxide solution, 3 g of tetrabutylammonium hydrogen sulphate and 16.5 g (80 mmol) of 2,6-difluorobenzylbromide. The mixture is stirred for 3 h at ambient temperature, the organic phase is separated off and the aqueous phase is extracted once with 100 ml of dichloromethane. The combined organic phases are washed once with 50 ml of 2 N hydrochloric acid, dried and the solvent is eliminated in vacuo. The residue is crystallised from diisopropylether. Yield: 23.5 g (85.1% of theory), melting point: 100° C.

Workup

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted once with 100 ml of dichloromethane
  3. washThe combined organic phases are washed once with 50 ml of 2 N hydrochloric acid
  4. customdried
  5. customThe residue is crystallised from diisopropylether

Sources & evidence

ORD record
ord-b6047a21df32412db13798d583ee3183
Source dataset
uspto-grants-2002_08
Patent number
US06441237B1

Reaction notes

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