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Formic Acid → (1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid

HRID 927893
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 927893
[CH2:1]([C@H:3]([O:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C:15]1[C:24]([C:25]([O:27]C)=[O:26])=[C:23]2[C:18]([C@H:19]3[CH2:29][C@H:20]3[CH2:21][O:22]2)=[CH:17][CH:16]=1)(=[O:13])=[O:12])[CH3:2].O.[OH-].[Li+].C(O)=O>O1CCOCC1.O.CO>[CH2:1]([C@H:3]([O:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C:15]1[C:24]([C:25]([OH:27])=[O:26])=[C:23]2[C:18]([C@H:19]3[CH2:29][C@H:20]3[CH2:21][O:22]2)=[CH:17][CH:16]=1)(=[O:12])=[O:13])[CH3:2]
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Komponenten

7

Edukt 3

HCID 284Formic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86713274methyl (1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzene-sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2×

Produkt 1

HCID 86713273(1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acidAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of methyl (1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzene-sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 213, 0.217 g) and lithium hydroxide monohydrate (0.168 g) in dioxane (3 mL) and water (1 mL) was irradiated in the microwave at 130° C. for 40 minutes. After cooling, the mixture was diluted with methanol, acidified with formic acid, evaporated in vacuo and azeotroped with a mixture of toluene and ethanol. The residue was triturated with 15% methanol in DCM, filtered and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-20%. The resultant gum was triturated with ether and ethyl acetate and filtered to give (1aR,7bS)-5-[2-((S)-1-ethylpyrrolidin-3-yloxymethyl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid (0.136 g) as a white solid.

Aufarbeitung

  1. customwas irradiated in the microwave at 130° C. for 40 minutes
  2. temperatureAfter cooling
  3. customevaporated in vacuo
  4. customazeotroped with a mixture of toluene and ethanol
  5. customThe residue was triturated with 15% methanol in DCM
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. customThe residue was purified by chromatography on silica
  9. washeluting with a mixture of methanol and DCM with a gradient of 0-20%
  10. customThe resultant gum was triturated with ether and ethyl acetate
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-612c176f4ac4462396f6e5d22bf59fb8
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09290472B2

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