Malic Acid → HCID 20092141、化合物

HRID 274185ノート

反応式

HRID 274185 の反応式
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]

参加物

9

反応物 5

HCID 525Malic AcidHCID 123472(Diethylamino)sulfur trifluorideHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridineHCID 20087472HCID 20087472、化合物HCID 20092120HCID 20092120、化合物

生成物 1

HCID 20092141HCID 20092141、化合物

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 6569Methyl Ethyl Ketone溶媒HCID 11430Potassium Carbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8fd6934632eb435faa314ac7bd2c8327
出典データセット
uspto-grants-1995_02
特許番号
US05389291

反応ノート

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