Acetone → (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732601
[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][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[C@@H:23]([OH:38])[C@@H:24]([NH:34][C:35](=[O:37])[CH3:36])[CH2:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:39][C:40]([CH3:42])=O.COC(C)=C>ClCCl>[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][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:10][C@@H:9]1[C@H:23]1[O:38][C:40]([CH3:42])([CH3:39])[N:34]([C:35](=[O:37])[CH3:36])[C@H:24]1[CH2:25][C:26]1[CH:27]=[C:28]([F:33])[CH:29]=[C:30]([F:32])[CH:31]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 83002-MethoxypropeneHCID 68814707(2R,4R)-2-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 68816295(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluorobenzyl)-2,2-dimethyloxazolidin-5-yl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 607,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add to a solution of (2R,4R)-2-[(1S,2S)-2-acetylamino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (5.64 g, 10.55 mmol) in dichloromethane (25 mL) and acetone (25 mL) p-toluene sulfonic acid pyridine salt (0.245 g, 1 mmol) and 2-methoxy propene (4.6 mL, 49 mmol). Stir 60 min and concentrate. Dissolve in ethyl acetate and wash with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate) and purify (silica gel chromatography, eluting with hexanes/ethyl acetate mixtures) to give the title compound as a foam (3.49 g, 61%).

Aufarbeitung

  1. concentrationconcentrate
  2. dissolutionDissolve in ethyl acetate
  3. washwash with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. custompurify
  6. wash(silica gel chromatography, eluting with hexanes/ethyl acetate mixtures)

Quellen und Nachweise

ORD-Eintrag
ord-5637c2c7aed64c0eaf3b5a657d5f73cc
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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