Malic Acid → HCID 19768421、化合物

HRID 1590850ノート

反応式

HRID 1590850 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[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])=[CH:17][C:16]=2[F:31])=[N:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].O1C(CCOCCC)C1.C(O)(=O)C(CC(O)=O)O.C(OC1C=CC(C2C=CC(O)=CC=2[F:71])=NC=1)CCCCCC.CCN(S(F)(F)F)CC>C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([F:71])[CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH3:29])=[CH:17][C:16]=2[F:31])=[N:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

参加物

9

反応物 5

HCID 525Malic AcidHCID 123472(Diethylamino)sulfur trifluorideHCID 19768417HCID 19768417、化合物HCID 20087472HCID 20087472、化合物HCID 135827543HCID 135827543、化合物

生成物 1

HCID 19768421HCID 19768421、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 5-heptyloxy-2-(4-(2-hydroxy-5-oxaoctyloxy)-2-fluorophenyl)pyridine (prepared by heating optically active 1,2-epoxy-5-oxaoctane, obtainable from malic acid, with 5-heptyloxy-2-(4-hydroxy-2-fluorophenyl)pyridine 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 to it dropwise with moisture being excluded. The reaction mixture is then stirred for 12 hours while heating slowly to room temperature. Then hydrolysis is carried out with ice cooling and the reaction mixture is washed with dilute sodium hydroxide solution and several times with water. After drying over magnesium sulfate, the solvent is removed on a rotary evaporator and the crude product is purified chromatographically and - by crystallization. Optically active 5-heptyloxy-2-(4-(2-fluoro-5-oxaoctyloxy)-2-fluorophenyl)pyridine is obtained.

後処理

  1. customThen hydrolysis
  2. washthe reaction mixture is washed with dilute sodium hydroxide solution and several times with water
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent is removed on a rotary evaporator
  5. customthe crude product is purified chromatographically and - by crystallization

出典と根拠

ORDレコード
ord-e719c0df00274ef3912b11a0240e50ac
出典データセット
uspto-grants-1993_04
特許番号
US05204476

反応ノート

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