Hydrochloric Acid → HCID 57786524, Verbindung

HRID 253599

Reaktionsgleichung

Reaktionsgleichung von HRID 253599
Cl.[NH2:2][C@@H:3]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C@H:4]([OH:9])[CH2:5][N:6]=[N+:7]=[N-:8].[CH3:17][O:18][C:19]1[C:20](=O)[C:21](=[O:25])[C:22]=1[O:23]C.C(N(CC)CC)C>C(#N)C>[N:6]([CH2:5][C@@H:4]([OH:9])[C@@H:3]([NH:2][C:20]1[C:21](=[O:25])[C:22](=[O:23])[C:19]=1[O:18][CH3:17])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[N+:7]=[N-:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 57462034HCID 57462034, Verbindung

Produkt 1

HCID 57786524HCID 57786524, VerbindungAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The HCl salt of (2R,3S)-3-amino-1-azido-4-cyclohexylbutan-2-ol (˜74 mg, 0.30 mmol) and 3,4-dimethoxycyclobut-3-ene-1,2-dione (70 mg, 0.49 mmol) were dissolved in acetonitrile (3 mL). Triethylamine (84 μL, 0.60 mmol) was added. The reaction was stirred at rt for 4 h. The solvent was evaporated and the crude material was redissolved in CH2Cl2. The solution was washed with 2% aq HCl, followed by brine, and dried over Na2SO4. The solution was filtered and the solvent removed under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with hexanes/EtOAc. 3-((2S,3R)-4-Azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-methoxycyclobut-3-ene-1,2-dione (63 mg) was isolated as a solid; MS m/z 323.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe crude material was redissolved in CH2Cl2
  3. washThe solution was washed with 2% aq HCl
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel eluting with hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-6d1c67a960744597a83df4fab35c423e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872028B2

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