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1,4-Dioxane → HCID 71186380, Verbindung

HRID 712919
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 712919
[CH3:1][C:2]1([CH3:34])[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[C@@H:4]([C:18]([NH:20][C:21]2([C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=3)[CH2:23][CH2:22]2)=[O:19])[CH2:3]1.O1CCOCC1.O[Li].O>O>[CH3:1][C:2]1([CH3:34])[CH2:6][N:5]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[C@@H:4]([C:18]([NH:20][C:21]2([C:24]3[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=3)[CH2:22][CH2:23]2)=[O:19])[CH2:3]1
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Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrate2×HCID 71204730HCID 71204730, Verbindung

Produkt 1

HCID 71186380HCID 71186380, VerbindungAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

(R)-methyl 4-(1-(4,4-dimethyl-1-(4-(trifluoromethyl)benzyl)pyrrolidine-2-carboxamido)cyclopropyl)benzoate (D151) (100 mg, 0.21 mmol) was partitioned between dioxane (2 ml) and water (2 ml) prior addition of LiOH H2O (35 mg, 0.84 mmol) and the resulting mixture was stirred at RT for 18 hrs. Dioxane was evaporated off and the aqueous solution acidified with acetic acid to pH˜4-5. A white solid precipitated which was filtered, dried under vacuum, then re-dissolved in dioxane (2 ml) and water (2 ml) and hydrolysed for additional 5 hrs after addition of LiOH H2O (18 mg, 0.42 mmol). Dioxane was evaporated off and the aqueous solution acidified with acetic acid to pH˜4-5. A white solid precipitated which was filtered and dried under vacuum, to afford the title compound (E34) (35.5 mg).

Aufarbeitung

  1. customDioxane was evaporated off
  2. customA white solid precipitated which
  3. filtrationwas filtered
  4. customdried under vacuum
  5. dissolutionre-dissolved in dioxane (2 ml)
  6. customDioxane was evaporated off
  7. customA white solid precipitated which
  8. filtrationwas filtered
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4fe5d63693114bfab4cd7e7f2aa34a4d
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181279B2

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