Malic Acid → HCID 19006685、化合物

HRID 1742561ノート

反応式

HRID 1742561 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[N: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=NC(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]=[N: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 19006688HCID 19006688、化合物HCID 20087472HCID 20087472、化合物HCID 136169458HCID 136169458、化合物

生成物 1

HCID 19006685HCID 19006685、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)pyrimidine (prepared by heating optically active 1,2-epoxy-5-oxaoctane, obtainable from malic acid, with 5-heptyloxy-2-(4-hydroxy-2-fluorophenyl)pyrimidine 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)pyrimidine 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-774950b6f0b44f8fae5b098ca217b904
出典データセット
uspto-grants-1994_08
特許番号
US05340497

反応ノート

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