Malic Acid → HCID 20092141, compound

HRID 274185Notes

Reaction equation

HRID 274185 reaction equation
C([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23](O)[CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH3:29])=[C:17]([F:31])[N:16]=1)CCCCCCC.O1C(CCOCCC)C1.C(O)(=O)C(CC(O)=O)O.[CH2:50]([O:58]C1C=CC(C2C=CC(O)=C(F)N=2)=CC=1)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57].CCN(S(F)(F)[F:79])CC>C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C.C(Cl)Cl>[CH2:50]([O:58][C:13]1[CH:14]=[CH:9][C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([F:79])[CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH3:29])=[C:17]([F:31])[N:16]=2)=[CH:11][CH:12]=1)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]

Participants

9

Reactant 5

HCID 525Malic AcidHCID 123472(Diethylamino)sulfur trifluorideHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridineHCID 20087472HCID 20087472, compoundHCID 20092120HCID 20092120, compound

Product 1

HCID 20092141HCID 20092141, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A solution of 0.1 mol of 2-(octylphenyl)-5-(2-hydroxy-5-oxaoctyloxy)-6-fluoropyridine (prepared by heating optically active 1,2-epoxy-5-oxaoctane, obtainable from malic acid, with 2C in the presence of dry potassium carbonate and methyl ethyl ketone as solvent) in methylene chloride is cooled to -40° C., and 0.11 mol of DAST is added dropwise thereto with exclusion of moisture. The reaction mixture is subsequently stirred for 12 hours with slow warming to room temperature. The reaction mixture is then hydrolyzed with ice cooling and washed with dilute sodium hydroxide solution and several times with water. The mixture is dried over magnesium sulfate, the solvent is removed on a rotary evaporator, and the crude product is purified by chromatography and by crystallization, giving optically active 2-(4-octyloxyphenyl)-5-(2-fluoro-5-oxaoctyloxy)-6-fluoropyridine.

Workup

  1. washhydrolyzed with ice cooling and washed with dilute sodium hydroxide solution and several times with water
  2. dry with materialThe mixture is dried over magnesium sulfate
  3. customthe solvent is removed on a rotary evaporator
  4. customthe crude product is purified by chromatography and by crystallization

Sources & evidence

ORD record
ord-8fd6934632eb435faa314ac7bd2c8327
Source dataset
uspto-grants-1995_02
Patent number
US05389291

Reaction notes

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