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Pyridine → tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide

HRID 2075415
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2075415
[S:1](Cl)(Cl)=[O:2].[Si:5]([O:12][C@@H:13]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1)[C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:15][OH:16])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].N1C=CC=CC=1>CC#N.C(Cl)Cl.C1COCC1>[Si:5]([O:12][C@@H:13]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=1)[C@H:14]1[CH2:15][O:16][S:1](=[O:2])[N:17]1[C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])([C:8]([CH3:9])([CH3:10])[CH3:11])([CH3:7])[CH3:6]
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Komponenten

7

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86636682tert-butyl (1S,2R)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Produkt 1

HCID 67089512tert-Butyl (4R)-4-((S)-((tert-butyl(dimethyl)silyl)oxy)(4-(trifluoromethyl)phenyl)methyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittel2×
HCID 6344DichloromethaneLösungsmittel2×
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of thionyl chloride (0.74 mL, 10.1 mmol) in MeCN (12 mL) and DCM (12 mL) at −78° C. was added a solution of tert-butyl (1S,2R)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (1.82 g, 4.05 mmol) in MeCN (20 mL), DCM (20 mL) and THF (4 mL) dropwise via a dropping funnel. After 10 minutes, pyridine (1.82 mL, 22.3 mmol) was added dropwise at −78° C. The mixture was allowed to warm to room temperature and stirred overnight. The solvent was removed in vacuo. The residue was taken up in EtOAc (60 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0%-10% EtOAc-hexane) to provide the product as a white solid (1.80 g, 90%).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0%-10% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cd11a6131eb14f6ca856fa22fb907999
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07919504B2

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