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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2357727
[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]
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Komponenten

7

Edukt 3

HCID 3440Furosemide2×HCID 6101p-Toluenesulfonic acidHCID 68457326(rac)-(R*,S*)-2-((2-hydroxy-(R)-1-methylethyl)amino)-1-(3,5-difluorophenyl)propanol

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241
Benzene
Lösungsmittel
3×
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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)]

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fdd6e9b5e1014390969b02c2afbb7b03
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07763612B2

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