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Potassium Carbonate → 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanol

HRID 1045074
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1045074
[CH2:1]1[C@@H:3]([NH3+:4])[C@H:2]1[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([F:12])[CH:6]=1.C1C=CC(C(O)C([O-])=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:31]1[C:32]2[N:43]=[N:42][N:41]([C@H:44]3[C@@H:48]4[O:49][C:50]([CH3:53])([CH3:52])[O:51][C@@H:47]4[C@@H:46]([O:54][CH2:55][CH2:56][OH:57])[CH2:45]3)[C:33]=2[N:34]=[C:35]([S:37][CH2:38][CH2:39][CH3:40])[N:36]=1>O>[F:12][C:7]1[CH:6]=[C:5]([C@@H:2]2[CH2:1][C@H:3]2[NH:4][C:31]2[C:32]3[N:43]=[N:42][N:41]([C@H:44]4[C@@H:48]5[O:49][C:50]([CH3:52])([CH3:53])[O:51][C@@H:47]5[C@@H:46]([O:54][CH2:55][CH2:56][OH:57])[CH2:45]4)[C:33]=3[N:34]=[C:35]([S:37][CH2:38][CH2:39][CH3:40])[N:36]=2)[CH:10]=[CH:9][C:8]=1[F:11]
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 210357742-(((3aR,4S,6R,6aS)-6-(7-Chloro-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanolHCID 66808833trans-(1r,2s)-2-(3,4-Difluorophenyl)cyclopropanaminium (2r)-2-hydroxy-2-phenylethanoate

Produkt 1

HCID 67289290
2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

trans-(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium (2R)-2-hydroxy-2-phenylethanoate (258 kg) and potassium carbonate (280 kg) were dissolved in water (1024 kg) and charged to the solution of 2-({(3aR,4S,6R,6aS)-6-[7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol solution from example 5 above with a rate that kept the temperature of the reaction ≦30° C. After full conversion was reached (≧99.9%) the water layer was separated off. The organic layer was washed with a mixture of acetic acid (96 kg) and sodium chloride (96 kg) in water (768 kg) and then washed again with a mixture of acetic acid (32 kg) and sodium chloride (22 kg) in water (952 kg). A third wash of the organic layer was done with sodium chloride (96 kg) in water (864 kg), whereafter the organic layer was used in the next step.

Aufarbeitung

  1. customthe temperature of the reaction ≦30° C
  2. customwas separated off
  3. washThe organic layer was washed with a mixture of acetic acid (96 kg) and sodium chloride (96 kg) in water (768 kg)
  4. washwashed again with a mixture of acetic acid (32 kg) and sodium chloride (22 kg) in water (952 kg)
  5. washA third wash of the organic layer

Quellen und Nachweise

ORD-Eintrag
ord-40bddbef90354835b0dedf9377105dda
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563755B2

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