Fumaric Acid → 2-Amino-8-hydroxymethyl-8-chloro-1,2,3,4-tetrahydronaphthalene fumarate

HRID 375584노트

반응식

HRID 375584 반응식
[NH2:1][C:2]1(CO)[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([Cl:12])[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[C:15]([C@:23]([C:38]([OH:40])=[O:39])(O)[C@:24](C(=O)C1C=CC=CC=1)(O)[C:25]([OH:27])=[O:26])(=[O:22])C1C=CC=CC=1.C(O)(=O)/C=C/C(O)=O>C(O)C>[C:38]([OH:40])(=[O:39])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[CH:8]=[CH:7][CH2:6][C:5]([CH2:15][OH:22])([Cl:12])[C:4]=2[CH2:3]1

참가 물질

5

반응물 3

HCID 444972Fumaric AcidHCID 100133902-Amino-2-hydroxymethyl-8-chloro-1,2,3,4-tetrahydronaphthaleneHCID 12362977Di-benzoyl-d-tartaric acid

생성물 1

HCID 867492202-Amino-8-hydroxymethyl-8-chloro-1,2,3,4-tetrahydronaphthalene fumarate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The expected product is obtained by resolving the compound obtained in stage D of Example 9 using (+)-dibenzoyl-D-tartaric acid by successive recrystallizations in ethanol. The enantiomeric purity is checked by chiral chromatography on a DIACEL-AD column, using an isopropanol/n-heptane/diethylamine mixture (40/1000/0.8) as eluent. The salt is then partitioned between 9N sodium hydroxide and dichloromethane. The aqueous phase is extracted with dichloromethane. After drying and evaporating the organic phases, the residue is dissolved in ethanol with one equivalent of fumaric acid and the mixture is brought to reflux. The expected product is then obtained after cooling, in the form of a white solid which is filtered off.

후처리

  1. customby successive recrystallizations in ethanol
  2. customThe salt is then partitioned between 9N sodium hydroxide and dichloromethane
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. customAfter drying
  5. customevaporating the organic phases
  6. temperatureto reflux

출처 및 근거

ORD 기록
ord-4dddc8347f1c4b08b74f867ac8c2bf7e
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486532

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