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Dimethyl Sulfoxide → tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-formyl-1,4-oxazepane-4-carboxylate

HRID 1022647
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1022647
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([C@H:19]2[C@H:25]([CH2:26][OH:27])[O:24][CH2:23][CH2:22][N:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20]2)[CH:15]=[CH:16][C:17]=1[Cl:18].O>C1COCC1.C(N(CC)CC)C>[Cl:11][C:12]1[CH:13]=[C:14]([C@H:19]2[C@H:25]([CH:26]=[O:27])[O:24][CH2:23][CH2:22][N:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20]2)[CH:15]=[CH:16][C:17]=1[Cl:18]
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Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 66975324tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate

Produkt 1

HCID 86663857tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-formyl-1,4-oxazepane-4-carboxylateAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8028TetrahydrofuranLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of oxalyl chloride (1.52 g) in THF (20 mL) was added dimethyl sulfoxide (1.87 g) at −78° C., and the mixture was stirred for 20 min. A solution of tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (3.0 g) in THF (10 mL) and triethylamine (7.78 mL) were added at −78° C., and the mixture was warmed to room temperature and stirred for 1 hr. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%)) to give the title compound (2.89 g) as a colorless solid.

Aufarbeitung

  1. stirringstirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%))

Quellen und Nachweise

ORD-Eintrag
ord-eae05214f4074e90ab220ec57e287eb7
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722662B2

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