Methanol → HCID 68816116, Verbindung

HRID 732372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732372
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][C:9](=N)[C:10](Cl)(Cl)Cl)=[CH:5][CH:4]=1.[CH3:17][O:18][C:19]([C@H:21]1[CH2:25][C@@H](O)C[N:22]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:20].CO>C1(C)C=CC=CC=1.[O-]S(C(F)(F)F)(=O)=O.[La+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[CH3:17][O:18][C:19]([C@H:21]1[CH2:25][C@@H:9]([O:8][CH2:7][C:6]2[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10][N:22]1[C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])=[O:20]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 110872634-Methoxybenzyl 2,2,2-Trichloroacetimidate

Produkt 1

HCID 68816116HCID 68816116, VerbindungAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2733938Lanthanum tris(trifluoromethanesulfonate)KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Add lanthanum triflate (3.6 g, 6.16 mmol) to a solution of 2,2,2-trichloro-acetimidic acid 4-methoxybenzyl ester (52.2 g, 185 mmol) and (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (30.2 g, 123 mmol) in toluene (200 mL). Stir 2.5 h, add methanol and concentrate. Dissolve in 25:75 dichloromethane:hexanes, filter away the insolubles and purify filtrate (silica gel chromatography, eluting with dichloromethane/ethyl acetate mixtures) to give the title compound (37.85 g, 84%).

Aufarbeitung

  1. concentrationconcentrate
  2. dissolutionDissolve in 25:75 dichloromethane
  3. filtrationhexanes, filter away the insolubles
  4. custompurify
  5. washfiltrate (silica gel chromatography, eluting with dichloromethane/ethyl acetate mixtures)

Quellen und Nachweise

ORD-Eintrag
ord-5b4d513008fa476ab107ad3badc70047
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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