Hydrochloric Acid → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl]cinnamic acid

HRID 473395노트

반응식

HRID 473395 반응식
[CH3:1][C:2]1([CH3:30])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH:14][C:15]([C:17]3[CH:29]=[CH:28][C:20]([CH:21]=[CH:22][C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=3)=[O:16])[CH:5]=[CH:4][C:3]1=2.O.[OH-].[Li+].Cl>CO.COCCOC.O>[CH3:1][C:2]1([CH3:30])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([NH:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[CH:28][CH:29]=3)=[O:16])[CH:5]=[CH:4][C:3]1=2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68431552Ethyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl]cinnamate

생성물 1

HCID 684324164-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl]cinnamic acid수율 95%

시약·촉매·용매 1

HCID 86709899methanol DME water용매

실험 절차

The above ester (109 mg, 0.269 mmol) was dissolved in methanol-DME-water (3:2:1, 4.2 ml), the solution was added with lithium hydroxide monohydrate (LiOH.H2O, 15 mg, 0.357 mmol), and the mixture was refluxed by heating for 1 hour. The mixture was cooled on ice, and then added with aqueous hydrochloric acid (1 N, 0.36 ml, 0.36 mmol), and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous sodium sulfate, and then the solvent was evaporated. The residue was recrystallized to obtain the title compound (96 mg, 95%) as colorless prisms.

후처리

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 1 hour
  3. temperatureThe mixture was cooled on ice
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was recrystallized

출처 및 근거

ORD 기록
ord-d2874e70987b41929b8b2d95f149df24
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633335B2

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