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Water → 3-(3-Bromobenzyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid (2,5-difluorophenyl)amide

HRID 1691655
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1691655
C(OC([N:8]1[CH2:26][CH2:25][C:11]2([O:15][C:14](=[O:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=3)[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[F:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1[N:42]=[C:43]=[O:44].O>C(Cl)Cl.CCOC(C)=O>[F:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1[NH:42][C:43]([N:8]1[CH2:26][CH2:25][C:11]2([O:15][C:14](=[O:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=3)[CH2:12]2)[CH2:10][CH2:9]1)=[O:44]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 27332661,4-Difluoro-2-isocyanatobenzeneHCID 576662773-(3-Bromobenzyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

Produkt 1

HCID 119922203-(3-Bromobenzyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid (2,5-difluorophenyl)amide

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound A6 (0.50 g, 1.18 mmol) was dissolved in DCM (3 mL) and combined with trifluoroacetic acid (3 mL). The reaction mixture was stirred for 5 min at RT and the solvent was then removed under a vacuum. The residue was combined repeatedly with toluene and the solvent was then removed again. The residue was then combined with sat. aq. NaHCO3 solution and repeatedly extracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was removed under a vacuum. The residue was redissolved in anhydrous THF (5 mL) and combined with a little triethylamine. The reaction mixture was combined with 2,5-difluorophenyl isocyanate (145 μL, 1.23 mmol), stirred for 18 h at RT and combined with water and EtOAc. The organic phase was separated off and the aqueous phase repeatedly extracted with EtOAc. The combined organic phases were washed with sat. aq. NaCl solution, dried over Na2SO4 and the solvent was removed under a vacuum. The residue was purified by column chromatography (SiO2, heptane/EtOAc 2:1). After crystallisation from heptane and DCM, 483 mg (85% of theoretical) of the desired product 3-(3-bromobenzyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid (2,5-difluorophenyl)amide (29) were obtained.

Aufarbeitung

  1. customthe solvent was then removed under a vacuum
  2. customthe solvent was then removed again
  3. extractionrepeatedly extracted with EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customthe solvent was removed under a vacuum
  6. dissolutionThe residue was redissolved in anhydrous THF (5 mL)
  7. stirringstirred for 18 h at RT
  8. customThe organic phase was separated off
  9. extractionthe aqueous phase repeatedly extracted with EtOAc
  10. washThe combined organic phases were washed with sat. aq. NaCl solution
  11. dry with materialdried over Na2SO4
  12. customthe solvent was removed under a vacuum
  13. customThe residue was purified by column chromatography (SiO2, heptane/EtOAc 2:1)
  14. customAfter crystallisation from heptane and DCM, 483 mg (85% of theoretical) of the desired product 3-(3-bromobenzyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid (2,5-difluorophenyl)amide (29)
  15. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-6cc35a32f1b14c9ca5c38ffd306d9208
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08153795B2

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