Water → HCID 86670468, Verbindung

HRID 1911851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911851
[H-].[Na+].[Si:3]([O:10][C@H:11]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C@H:12]1[CH2:16][CH2:15][C@@H:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:34])[NH:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:20][CH:19]=2)[N:13]1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].I[CH3:49].O>O1CCCC1>[Si:3]([O:10][C@H:11]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C@H:12]1[CH2:16][CH2:15][C@@H:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:34])[N:25]([CH3:49])[CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:20][CH:19]=2)[N:13]1[C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])([C:6]([CH3:7])([CH3:8])[CH3:9])([CH3:4])[CH3:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86670467HCID 86670467, Verbindung

Produkt 1

HCID 86670468HCID 86670468, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (8.38 mg of a 60 wt % dispersion in mineral oil, 0.210 mmol) was added to a stirred, room temperature mixture of tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-(4-{[2-(pyridine-2-yl)ethyl]carbamoyl}benzyl)pyrrolidine-1-carboxylate (120 mg, 0.191 mmol) in tetrahydrofuran (1.9 mL), and the mixture was stirred for 30 minutes. After 30 minutes, iodomethane (0.014 mL, 0.23 mmol) was added and the mixture was stirred for 12 hours. Water was then added and the mixture was partitioned with EtOAc. The aqueous extracts were extracted with EtOAc (3×), and the combined organic layers were washed with brine, dried with Na2SO4, filtered, and concentrated in vacuo to give the product as an orange oil that was used directly in the next step. LC-MS=644.3 (M+1)+.

Aufarbeitung

  1. waitAfter 30 minutes
  2. stirringthe mixture was stirred for 12 hours
  3. customthe mixture was partitioned with EtOAc
  4. extractionThe aqueous extracts were extracted with EtOAc (3×)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0654e0d8da83409bb95126238997e636
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604038B2

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