Diethylamine → methyl (1aRS,7bSR)-5-{N-(methoxycarbonyl)-N-[2((Z)-4-diethylaminobut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

HRID 927958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927958
CS(OS(C)(=O)=O)(=O)=O.[CH3:10][O:11][C:12]([N:14]([C:30]1[C:39]([C:40]([O:42][CH3:43])=[O:41])=[C:38]2[C:33]([CH:34]3[CH2:44][CH:35]3[CH2:36][O:37]2)=[CH:32][CH:31]=1)[S:15]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1/[CH:25]=[CH:26]\[CH2:27][CH2:28]O)(=[O:17])=[O:16])=[O:13].[CH:45]([N:48](C(C)C)[CH2:49][CH3:50])(C)[CH3:46].C(NCC)C>C(Cl)Cl.O>[CH3:10][O:11][C:12]([N:14]([C:30]1[C:39]([C:40]([O:42][CH3:43])=[O:41])=[C:38]2[C:33]([CH:34]3[CH2:44][CH:35]3[CH2:36][O:37]2)=[CH:32][CH:31]=1)[S:15]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1/[CH:25]=[CH:26]\[CH2:27][CH2:28][N:48]([CH2:49][CH3:50])[CH2:45][CH3:46])(=[O:17])=[O:16])=[O:13]

Komponenten

7

Edukt 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 86713307Methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-4-hydroxybut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×

Produkt 1

HCID 90086604methyl (1aRS,7bSR)-5-{N-(methoxycarbonyl)-N-[2((Z)-4-diethylaminobut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylateAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl sulfonic anhydride (0.062 g) was added to a stirred, cooled mixture of methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-4-hydroxybut-1-enyl)-4-fluorobenzene-sulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 73, 0.12 g) and N,N-di-isopropyl-N-ethylamine (0.046 g) in DCM (15 mL) at 0° C. The resultant mixture was stirred at 0° C. for 20 minutes. Diethylamine (0.026 g) was added and the mixture was then stirred at room temperature for 24 hours. The mixture was diluted with water and extracted with DCM, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 2-10% to give methyl (1aRS,7bSR)-5-{N-(methoxycarbonyl)-N-[2((Z)-4-diethylaminobut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (0.08 g) as alight yellow solid.

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted with DCM
  3. dry with materialdried (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 methanol and DCM with a gradient of 2-10%

Quellen und Nachweise

ORD-Eintrag
ord-dfa2be822814449a8245921e9eb5ad85
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

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