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Acetic Acid → 1,1-Dimethylethyl N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamate

HRID 711309
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 711309
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[C@@H:14]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][CH:12]([OH:23])[CH2:11][O:10]1.C(#N)C.C(O)(=O)C.CC(O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[C@@H:14]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:13][C:12](=[O:23])[CH2:11][O:10]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 6342AcetonitrileHCID 86713019(2ξ,5R)-1,5-Anhydro-3,4-dideoxy-5-C-(2,5-difluorophenyl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-D-glycero-pentitol

Produkt 1

HCID 441939251,1-Dimethylethyl N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 46.8 kg (142 mol) of tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbamate in a stirred vessel was added acetonitrile (150 kg), acetic acid (50 kg), and water (25 kg). After dissolving at room temperature, the solution was cooled to 0° C. and RuCl3.3H2O (250 g, 956 mmol) in water (50 kg) was added under nitrogen. Then, NaBrO3 (11.7 kg, 77.5 mol) was added in six portions every 1.5 h under nitrogen. After stirring at 0° C. for 6 h, 2-propanol (31 kg) was added over 30 min. at 0° C. Then, water (720 kg) was added at this temperature over 5 h. The resulting slurry was stirred overnight, filtered, and cake washed with water. The solids were then dried under vacuum at 40-60° C. to give tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl]carbamate.

Aufarbeitung

  1. dissolutionAfter dissolving at room temperature
  2. stirringThe resulting slurry was stirred overnight
  3. filtrationfiltered
  4. washcake washed with water
  5. customThe solids were then dried under vacuum at 40-60° C.

Quellen und Nachweise

ORD-Eintrag
ord-5460b42a0d3d44899ee667f89be1fd57
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181262B2

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