Hydroxylamine → HCID 87348653, Verbindung

HRID 61492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61492
[CH2:1]([C@:8]12[CH2:16][C@H:12]([C:13](=[O:15])[O:14]1)[C@@H:11]([C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]1)=[O:18])[CH2:10][CH2:9]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:31][OH:32]>CO>[CH2:1]([C@@:8]1([OH:14])[CH2:16][C@H:12]([C:13]([NH:31][OH:32])=[O:15])[C@@H:11]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 787HydroxylamineHCID 67304651HCID 67304651, Verbindung

Produkt 1

HCID 87348653HCID 87348653, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a stirred solution of (1S,2S,5S)-5-benzyl-2-[(4-phenylpiperazin-1-yl)carbonyl]-6-oxabicyclo[3.2.1]-octan-7-one (8.0 mg, 0.020 mmol) in anhydrous methanol (1.0 mL, 0.025 mol) at rt was added 1.50 M of hydroxylamine in methanol (0.396 mL). The reaction mixture was stirred at rt for 3 h. The reaction was quenched with saturated aqueous NH4Cl (15 mL), extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC with 5-95% MeCN/H2O (with 0.05% TFA) to give the pure product as a colorless solid (2.3 mg, 26% in yield). MS (ESI): (M+H)+=438.1.

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NH4Cl (15 mL)
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC with 5-95% MeCN/H2O (with 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-a84c64821f634b04b8f6e33e9767a318
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440958B2

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