Malic Acid → HCID 19006685, Verbindung

HRID 1742561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742561
[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]

Komponenten

9

Edukt 5

HCID 525Malic AcidHCID 123472(Diethylamino)sulfur trifluorideHCID 19006688HCID 19006688, VerbindungHCID 20087472HCID 20087472, VerbindungHCID 136169458HCID 136169458, Verbindung

Produkt 1

HCID 19006685HCID 19006685, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-774950b6f0b44f8fae5b098ca217b904
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05340497

Notizen zur Reaktion

Wird geladen…