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Hydrochloric Acid → Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-formylcyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate

HRID 1746626
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1746626
C(N(CC)CC)C.CS(C)=O.[C:12]([O:15][C@H:16]1[CH2:20][CH2:19][C@H:18]([CH2:21][OH:22])[C@H:17]1[CH2:23][CH2:24][S:25][C:26]1[S:27][CH:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:30]=1)(=[O:14])[CH3:13].Cl>C(OCC)(=O)C>[C:12]([O:15][C@H:16]1[CH2:20][CH2:19][C@H:18]([CH:21]=[O:22])[C@H:17]1[CH2:23][CH2:24][S:25][C:26]1[S:27][CH:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:30]=1)(=[O:14])[CH3:13]
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 15979344Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-(hydroxymethyl)cyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate

Produkt 1

HCID 86634273Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-formylcyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylateAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triethylamine (3.7 mL) and sulfur trioxide•pyridine complex (1.7 g) were added to a dimethyl sulfoxide(4.0 mL)/ethyl acetate(8.0 mL) solution of ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-(hydroxymethyl)cyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylate (500 mg) (see compound 7 described in the pamphlet of International Publication No. WO 2006/129788) at 10° C., followed by stirring at room temperature for 30 min. To the reaction solution, 1 N hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine; dried with anhydrous sodium sulfate; and concentrated to obtain the title compound (497 mg) having the following physical properties:

Aufarbeitung

  1. customat 10° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationand concentrated

Quellen und Nachweise

ORD-Eintrag
ord-dbef88a1017f48afa9028958767345c4
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150528B2

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