Potassium Carbonate → HCID 86622359, Verbindung

HRID 501748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501748
Br[CH2:2][C@@H:3]([OH:25])[C@@H:4]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:13][C:8]1[CH:7]=[C:6]([CH2:5][C@H:4]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:3]2[CH2:2][O:25]2)[CH:11]=[C:10]([Cl:12])[CH:9]=1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 86622360HCID 86622360, Verbindung

Produkt 1

HCID 86622359HCID 86622359, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Step BF (7): To a suspension of benzyl (2S,3S)-4-bromo-1-(3,5-dichlorophenyl)-3-hydroxybutan-2-ylcarbamate (100 mg, 224 umol) in MeOH (2.4 mL) was added K2CO3 (12 mg). The reaction was stirred vigorously overnight. Solvents were removed in vacuo, and the residue partitioned between EtOAc and water three times. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the solid benzyl (S)-2-(3,5-dichlorophenyl)-1-((S)-oxiran-2-yl)ethylcarbamate (78.9 mg, 97% yield). 1H NMR (DMSO-d6) δ 7.08-7.55 (m, 9H) 4.99 (d, J=12.8 Hz, 1H) 4.89 (d, J=12.8 Hz, 1H) 3.60-3.78 (m, 1H) 2.89-3.06 (m, 2H) 2.60-2.79 (m, 3H).

Aufarbeitung

  1. customSolvents were removed in vacuo
  2. customthe residue partitioned between EtOAc and water three times
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5e7abb4418574323abfba3442f894d8d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772221B2

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