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Ammonium Chloride → 5-(S)-Azidomethyl-3-[4'-aminocarbonyl-3'-fluorophenyl]oxazolidine-2-one

HRID 2305659
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2305659
[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17](O)=[O:18])=[C:13]([F:20])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].F[P-](F)(F)(F)(F)F.[N:28]1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C=O)C>[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH2:28])=[O:18])=[C:13]([F:20])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3]
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Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 229662095-(S)-azidomethyl-3-(4'-carboxy-3'-fluorophenyl)oxazolidine-2-one

Produkt 1

HCID 22966208
5-(S)-Azidomethyl-3-[4'-aminocarbonyl-3'-fluorophenyl]oxazolidine-2-one
Ausbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-(S)-azidomethyl-3-[4′-carboxy-3′-fluorophenyl-]oxazolidine-2-one (3.2 g, 11.4 mmol; prepared as described in Example 3), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (6.5 g, 17.1 mmole) and N,N′-diisopropylethylamine (5.9 g, 7.9 ml, 45.6 mmol) in DMF (12 ml) was stirred at room temperature for 20 min. Ammonium chloride (1.2 g, 22.8 mmol) was added, and the reaction mixture was stirred at r. t. overnight. Most of the solvent was removed under vacuum, and the residue taken up in ethyl acetate and washed twice with 3% aq. citric acid and brine. Organic layer was dried (Na2SO4) and concentrated under vacuum. Crude material was purified by silica gel chromatography eluting with 15% methanol in ethyl acetate to afford a white crystalline product (2.8 g, 91%). HPLC Rt=4.7, MS (m/z): [M+H]+=280.

Aufarbeitung

  1. customovernight
  2. customMost of the solvent was removed under vacuum
  3. washwashed twice with 3% aq. citric acid and brine
  4. dry with materialOrganic layer was dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customCrude material was purified by silica gel chromatography
  7. washeluting with 15% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c7160594f8c14e549fd72e4d68eedf61
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06441005B1

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