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1-Methylimidazole → HCID 58712131, Verbindung

HRID 1528515
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1528515
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])[CH3:3].CN1C=CN=C1.Cl.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[N:30][O:31][C:32]=2[C:33]2[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH3:42])=[C:35]([O:43][CH3:44])[CH:34]=2)=[CH:24][C:23]=1[NH2:45]>C1COCC1>[C:2]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:12])[NH:45][C:23]1[CH:24]=[C:25]([C:28]2[CH:29]=[N:30][O:31][C:32]=2[C:33]2[CH:34]=[C:35]([O:43][CH3:44])[C:36]([O:41][CH3:42])=[C:37]([O:39][CH3:40])[CH:38]=2)[CH:26]=[CH:27][C:22]=1[O:21][CH3:20])([CH3:1])([CH3:3])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 13901-MethylimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 66929481HCID 66929481, Verbindung

Produkt 1

HCID 58712131HCID 58712131, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of N-t-Boc-glycine (357 mg, 2 mmol) and N-methyl-imidazole (0.162 mL, 2 mmol) in THF (16 mL) cooled with ice methanesulfonyl chloride (0.158 mL, 2 mmol) was added. Ice batch was removed, compound 5 (0.4 g, 1 mmol) was added as a solid, followed by thriethylamine (0.144 mL, 2.02 mmol), and the reaction mixture was stirred at 40-50° C. overnight. A resulted solution was decanted from a solid, a flask rinsed with EtOAc, and a combined organic solution was washed with saturated ammonium chloride solution, then twice with water, brine and dried over anhydrous sodium sulfate. The solution was filtered out through a celite pad, concentrated and the residue was dissolved in 2-propanol (3 mL) with heating, and hexane (1-2 mL) was added drop-wise to start precipitation. In 1 hour a solid was filtered out, washed with 1:1 Hexane:ether mixture (10 ml×2) and vacuum-dried to give compound 6, 0.49 g (93.7%), LC purity 99%. 1H NMR (DMSO-d6): δ 9.11 (s, 1H), 8.81 (s, 1H), 8.22 (s, 1H), 7.24 (m, 1H), 7.20-7.15 (m, 2H), 6.91 (s, 2H), 3.87 (s, 3H), 3.73 (m, 2H), 3.70 (s, 3H), 3.66 (s, 6H). 1.40 (s, 9H).

Aufarbeitung

  1. additionwas added
  2. customIce batch was removed
  3. customA resulted solution was decanted from a solid, a flask
  4. washrinsed with EtOAc
  5. washa combined organic solution was washed with saturated ammonium chloride solution
  6. dry with materialtwice with water, brine and dried over anhydrous sodium sulfate
  7. filtrationThe solution was filtered out through a celite pad
  8. concentrationconcentrated
  9. dissolutionthe residue was dissolved in 2-propanol (3 mL)
  10. temperaturewith heating
  11. additionhexane (1-2 mL) was added drop-wise
  12. customprecipitation
  13. filtrationIn 1 hour a solid was filtered out
  14. washwashed with 1:1 Hexane
  15. dry with materialether mixture (10 ml×2) and vacuum-dried

Quellen und Nachweise

ORD-Eintrag
ord-c73921305dd942a8864e4cb840fe6548
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090603B2

Notizen zur Reaktion

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