2-Methoxypropane → (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-benzyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732379
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[C@@H:21]([OH:36])[C@@H:22]([NH:32][C:33](=[O:35])[CH3:34])[CH2:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][C:38]1C=CC(S([O-])(=O)=O)=C[CH:39]=1.C1C=C[NH+]=CC=1.COC(C)C>ClCCl.CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][C@@H:9]1[C@H:21]1[O:36][C:38]([CH3:39])([CH3:37])[N:32]([C:33](=[O:35])[CH3:34])[C@H:22]1[CH2:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 117212-MethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 68817282(2R,4R)-2-[(1S,2S)-2-Acetylamino-3-(3,5-difluoro-phenyl)-1-hydroxy-propyl]-4-benzyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 68814284(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-benzyloxy-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 734,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584124Propan-2-one--dichloromethane (1/1)Lösungsmittel

Versuchsvorschrift

Dissolve (2R,4R)-2-[(1S,2S)-2-Acetylamino-3-(3,5-difluoro-phenyl)-1-hydroxy-propyl]-4-benzyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.150 g, 0.3 mmol) in 1:1 dichloromethane/acetone (5 mL). Add PPTS (pyridine/p-toluene sulfonic acid) (0.03 mmol) and 2-methoxypropane (1.5 mmol). When the reaction is complete by TLC (15 minutes), concentrate the reaction mixture under reduced pressure. Dissolve the residue in ethyl acetate and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. Dry over magnesium sulfate, concentrate under reduced pressure, and subject the residue to silica gel chromatography, eluting with ethyl acetate/hexane to provide the desired compound (0.120 g, 75%).

Aufarbeitung

  1. customis complete by TLC (15 minutes)
  2. concentrationconcentrate the reaction mixture under reduced pressure
  3. dissolutionDissolve the residue in ethyl acetate
  4. washwash with saturated aqueous sodium bicarbonate
  5. dry with materialDry over magnesium sulfate
  6. concentrationconcentrate under reduced pressure
  7. washeluting with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-f840b3c87d344e82962d2d74ddff01fe
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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