Methanol → {(5S)-3-[3,5-difluoro-4-(6-oxa-3-azabicyclo[3.1.0]hex-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl acetamide

HRID 1814035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814035
[O-][CH2:2][CH2:3]CC.[Li+].C([O:14][C:15](=[O:31])[NH:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([N:24]2[CH2:29][CH:28]3[CH:26]([O:27]3)[CH2:25]2)=[C:19]([F:30])[CH:18]=1)C1C=CC=CC=1.C[OH:33].C([NH:37][CH2:38][C@H:39](OC(=O)C)[CH2:40]Cl)(=O)C>CN(C=O)C.C1COCC1>[F:30][C:19]1[CH:18]=[C:17]([N:16]2[CH2:3][C@H:2]([CH2:40][CH2:39][C:38]([NH2:37])=[O:33])[O:14][C:15]2=[O:31])[CH:22]=[C:21]([F:23])[C:20]=1[N:24]1[CH2:25][CH:26]2[CH:28]([O:27]2)[CH2:29]1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 7357675(2S)-1-Acetamido-3-chloropropan-2-yl acetateHCID 20770994[3,5-Difluoro-4-(6-oxa-3-aza-bicyclo[3.1.0]hex-3-yl)-phenyl]-carbamic acid benzyl esterHCID 23676864Lithium butan-1-olate

Produkt 1

HCID 86593189{(5S)-3-[3,5-difluoro-4-(6-oxa-3-azabicyclo[3.1.0]hex-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium butoxide solution (1.9 mL of a 1.0 M THF solution, 1.9 mmol) was added to a cooled (0° C.) solution of [3,5-difluoro-4-(6-oxa-3-aza-bicyclo[3.1.0]hex-3-yl)-phenyl]-carbamic acid benzyl ester (0.22 g, 0.64 mmol) in DMF (0.43 mL) and MeOH (0.05 mL, 1.2 mmol). Solid (S)-acetic acid 2-acetylamino-1-chloromethyl-ethyl ester (0.25 g, 1.27 mmol) was then added and the solution allowed to warm to room temperature and stirred for 16 h. The reaction mixture was quenched with sat. NH4Cl and extracted with ethyl acetate. The organic layers were washed with water, brine and dried (MgSO4). The title compound was isolated by silica gel chromatography (0-3% MeOH/dichloromethane).

Aufarbeitung

  1. customThe reaction mixture was quenched with sat. NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-e08a53b80d5c4aae8b12e116d32cbe4c
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875784B2

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