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Triethylamine → HCID 178470087, Verbindung

HRID 1093075
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1093075
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:20]2[NH:21][C:22](=O)[C:23]([OH:31])=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:20]2[NH:21][CH2:22][C:23]([O:31][S:34]([CH3:33])(=[O:36])=[O:35])=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:17][CH2:16][CH:15]([CH2:18][O:19][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 136061329HCID 136061329, Verbindung

Produkt 1

HCID 178470087HCID 178470087, VerbindungAusbeute 815,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 2-(1-(benzyloxycarbonylamino)-4-(hydroxymethyl)cyclohexyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.85 g, 4.15 mmol) in THF (40 mL) cooled to 0° C. was added methanesulfonyl chloride (0.96 mmol, 12.45 mmol) and triethylamine (1.79 mL, 12.87 mmol). The mixture was allowed to warm to room temperature and stirred for 18 h. The resulting precipitate was filtered off and washed with THF. The filtrate and washings were concentrated to afford an amber oil. A solution of this oil in methanol (10 mL) was treated with K2CO3 (574 mg, 4.15 mmol) at room temperature for 3 h. The mixture was then concentrated and the residue was dissolved in ethyl acetate (200 mL), washed with 1N HCl (100 mL) followed by brine (100 mL), then dried (Na2SO4), filtered and concentrated to give 2.3 g of title compound as a yellow oil. LCMS (M+H)=602.45.

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with THF
  3. concentrationThe filtrate and washings were concentrated
  4. customto afford an amber oil
  5. concentrationThe mixture was then concentrated
  6. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  7. washwashed with 1N HCl (100 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e81b67721eaf42ca9336a422de6a6a52
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129398B2

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