Malic Acid → HCID 20092141, 화합물

HRID 274185노트

반응식

HRID 274185 반응식
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]

참가 물질

9

반응물 5

HCID 525Malic AcidHCID 123472(Diethylamino)sulfur trifluorideHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridineHCID 20087472HCID 20087472, 화합물HCID 20092120HCID 20092120, 화합물

생성물 1

HCID 20092141HCID 20092141, 화합물

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 6569Methyl Ethyl Ketone용매HCID 11430Potassium Carbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8fd6934632eb435faa314ac7bd2c8327
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389291

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