Hydrochloric Acid → Hydroxy Tipelukast

HRID 486122노트

반응식

HRID 486122 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH2:22][CH2:23][CH3:24])=[C:8]([C:16]([CH:19]([OH:21])[CH3:20])=[CH:17][CH:18]=1)[O:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[OH:25][C:26]1[C:31]([CH2:32][CH2:33][CH3:34])=[C:30]([SH:35])[CH:29]=[CH:28][C:27]=1[C:36](=[O:38])[CH3:37].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:36]([C:27]1[CH:28]=[CH:29][C:30]([S:35][CH2:2][CH2:3][CH2:4][O:5][C:6]2[C:7]([CH2:22][CH2:23][CH3:24])=[C:8]([C:16]([CH:19]([OH:21])[CH3:20])=[CH:17][CH:18]=2)[O:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[C:31]([CH2:32][CH2:33][CH3:34])[C:26]=1[OH:25])(=[O:38])[CH3:37]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-oneHCID 54321325HCID 54321325, 화합물

생성물 1

HCID 9828483Hydroxy Tipelukast수율 35.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixed solution of 55.9 mg of (-)-4-[3-(3-chloropropoxy)-6-(1-hydroxyethyl)-2-propylphenoxy] butanoic acid, 39.3 mg of (2-hydroxy-4-mercapto-3-propylphenyl) ethanone, 51.7 mg of potassium carbonate and 1 ml of dimethylformamide was stirred at room temperature for 6 hours. The reaction mixture was poured into ice water, acidified with 1N-hydrochloric acid, and extracted with ethyl acetate. After washed with water and saturated aqueous solution of sodium chloride, the organic layer was dried over anhydrous sodium sulfate and subjected to distillation off of the solvent under reduced pressure to afford residue, which was then purified through silica gel column chromatography (methylene chloride: methanol=20:1) and further purified through preparative thin layer chromatography (methylene chloride: methanol=15:1) to afford 29.8 mg of yellow oily matter as the title compound (35.9%). [α]D20 -13.8° (c=2.98, ethanol)

후처리

  1. extractionextracted with ethyl acetate
  2. washAfter washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. distillationsubjected to distillation off of the solvent under reduced pressure
  5. customto afford residue, which
  6. customwas then purified through silica gel column chromatography (methylene chloride: methanol=20:1)
  7. customfurther purified through preparative thin layer chromatography (methylene chloride: methanol=15:1)

출처 및 근거

ORD 기록
ord-53511a9e05cd4d08b7bab8f742ccf7e2
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290812

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