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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Furosemide → (rac)-(R*,S*)-2-((2-(3,5-difluorophenyl)-2-hydroxy-1-methylethyl)amino)-(R)-2-methylethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate

HRID 2357727
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HRID 2357727 반응식
[OH:1][CH2:2][C@H:3]([NH:5][C@@H:6]([CH3:17])[C@@H:7]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)[OH:8])[CH3:4].[CH:18]1[CH:19]=[C:20]([CH2:23][NH:24][C:25]2[C:30]([C:31](O)=[O:32])=[CH:29][C:28]([S:34]([NH2:37])(=[O:36])=[O:35])=[C:27]([Cl:38])[CH:26]=2)[O:21][CH:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1C=CC=CC=1.C1(C)C=CC=CC=1>[NH2:37][S:34]([C:28]1[C:27]([Cl:38])=[CH:26][C:25]([NH:24][CH2:23][C:20]2[O:21][CH:22]=[CH:18][CH:19]=2)=[C:30]([CH:29]=1)[C:31]([O:1][CH2:2][C@H:3]([NH:5][C@H:6]([CH3:17])[C@H:7]([C:9]1[CH:10]=[C:11]([F:16])[CH:12]=[C:13]([F:15])[CH:14]=1)[OH:8])[CH3:4])=[O:32])(=[O:35])=[O:36]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 3440Furosemide2회HCID 6101p-Toluenesulfonic acidHCID 68457326(rac)-(R*,S*)-2-((2-hydroxy-(R)-1-methylethyl)amino)-1-(3,5-difluorophenyl)propanol

생성물 1

HCID 131728258(rac)-(R*,S*)-2-((2-(3,5-difluorophenyl)-2-hydroxy-1-methylethyl)amino)-(R)-2-methylethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate

시약·촉매·용매 3

HCID 241
Benzene
용매
3회
HCID 962Water용매
HCID 1140Toluene용매

실험 절차

The free base of (rac)-(R*,S*)-2-((2-hydroxy-(R)-1-methylethyl)amino)-1-(3,5-difluorophenyl)propanol (21) (0.023 mole) and benzene (30 mL) (or toluene) is added to a round-bottomed flask. Furosemide (5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid (10), (Aldrich) (0.025 mole), benzene (30 mL), and p-toluenesulfonic acid (0.026 mole) catalyst is added to the flask. A Dean-Stark trap is filled with benzene, and the contents of the flask is refluxed with stirring for several hours or until no additional water is collected in the trap. The reaction is cooled, extracted with sodium bicarbonate solution, washed with water, and then with a saturated sodium chloride solution. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo to give crude product, which may be purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent. The fractions that contain pure product may be combined and spin evaporated in vacuo to give a solid that may be recrystallized to give (rac)-(R*,S*)-2-((2-(3,5-difluorophenyl)-2-hydroxy-1-methylethyl)amino)-(R)-2-methylethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate (210). [See eg., Sandier et al., Organic Functional Group Preparations, p. 249 (1968)]

후처리

  1. temperaturethe contents of the flask is refluxed
  2. customis collected in the trap
  3. temperatureThe reaction is cooled
  4. extractionextracted with sodium bicarbonate solution
  5. washwashed with water
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give crude product, which
  10. custommay be purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent
  11. customspin evaporated in vacuo
  12. customto give a solid
  13. customthat may be recrystallized

출처 및 근거

ORD 기록
ord-fdd6e9b5e1014390969b02c2afbb7b03
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07763612B2

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