Malic Acid → HCID 19768421, 화합물

HRID 1590850노트

반응식

HRID 1590850 반응식
[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]

참가 물질

9

반응물 5

HCID 525Malic AcidHCID 123472(Diethylamino)sulfur trifluorideHCID 19768417HCID 19768417, 화합물HCID 20087472HCID 20087472, 화합물HCID 135827543HCID 135827543, 화합물

생성물 1

HCID 19768421HCID 19768421, 화합물

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 6569Methyl Ethyl Ketone용매HCID 11430Potassium Carbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e719c0df00274ef3912b11a0240e50ac
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05204476

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