Pyridine → methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927992
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([CH:6]3[CH2:16][CH:7]3[CH2:8][O:9]2)=[CH:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=1.N1C=CC=CC=1>C(Cl)Cl>[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:1][C:2]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]3[C:5]([CH:6]4[CH2:16][CH:7]4[CH2:8][O:9]3)=[CH:4][CH:3]=2)(=[O:26])=[O:25])=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 27590464-Fluoro-2-nitrobenzene-1-sulfonyl chlorideHCID 86713293Methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×

Produkt 1

HCID 86713325methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylateAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of methyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (Intermediate 42, 0.1 g), 4-fluoro-2-nitrobenzenesulfonyl chloride (0.115 g) and pyridine (2 mL) in DCM (5 mL) was stirred at room temperature overnight. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether (20%) to give methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.11 g) as a yellow oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and petroleum ether (20%)

Quellen und Nachweise

ORD-Eintrag
ord-496fb99a84044b1e8924143a7f6243a2
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

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