Acetic Acid → methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(2-amino-4-fluorobenzenesulfonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927990
[CH3:1][O:2][C:3]([N:5]([C:19]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]2[C:22]([CH:23]3[CH2:33][CH:24]3[CH2:25][O:26]2)=[CH:21][CH:20]=1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[N+:16]([O-])=O)(=[O:8])=[O:7])=[O:4].C(O)(=O)C>C(O)C.[Zn]>[CH3:1][O:2][C:3]([N:5]([C:19]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]2[C:22]([CH:23]3[CH2:33][CH:24]3[CH2:25][O:26]2)=[CH:21][CH:20]=1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[NH2:16])(=[O:7])=[O:8])=[O:4]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 86713324methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(4-fluoro-2-nitrobenzene-sulfonyl)amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate2×

Produkt 1

HCID 86713323methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(2-amino-4-fluorobenzenesulfonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(4-fluoro-2-nitrobenzene-sulfonyl)amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (Intermediate 111, 0.2 g), zinc (0.54 g) and acetic acid (0.5 g) in ethanol (20 mL) was stirred and heated at reflux for 1 hour. After cooling, the solid was filtered off and the filtrate was evaporated to dryness. The residue was treated with saturated aqueous sodium bicarbonate and extracted with ethyl acetate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether with a gradient of 30-50% to give methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(2-amino-4-fluorobenzenesulfonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.15 g) as a white solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered off
  5. customthe filtrate was evaporated to dryness
  6. additionThe residue was treated with saturated aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customthe residue was purified by chromatography on silica
  12. washeluting with a mixture of ethyl acetate and petroleum ether with a gradient of 30-50%

Quellen und Nachweise

ORD-Eintrag
ord-3274b17c794d4592ba07e9833e17a138
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

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