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Ammonium Chloride → 4-Hydroxy-8-methoxy-1-(tetrahydro-furan-2-yloxy)-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

HRID 1473781
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1473781
CO[C:3]([C:5]1([N:13]([O:26][CH:27]2[CH2:31][CH2:30][CH2:29][O:28]2)[C:14](=[O:25])[CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[CH2:10][CH2:9][N:8]([O:11][CH3:12])[CH2:7][CH2:6]1)=[O:4].C[O-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[OH:4][C:3]1[C:5]2([CH2:6][CH2:7][N:8]([O:11][CH3:12])[CH2:9][CH2:10]2)[N:13]([O:26][CH:27]2[CH2:31][CH2:30][CH2:29][O:28]2)[C:14](=[O:25])[C:15]=1[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24]
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Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 584280531-Methoxy-4-{(tetrahydro-furan-2-yloxy)-[2-(2,4,6-trimethyl-phenyl)-acetyl]-amino}-piperidine-4-carboxylic acid methyl ester

Produkt 1

HCID 584280204-Hydroxy-8-methoxy-1-(tetrahydro-furan-2-yloxy)-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 1-methoxy-4-{(tetrahydro-furan-2-yloxy)-[2-(2,4,6-trimethyl-phenyl)-acetyl]-amino}-piperidine-4-carboxylic acid methyl ester (70 g, 161.1 mmol) in dimethylformamide (350 ml) at 10° C. was added sodium methoxide (26.9 g, 483.3 mmol) in four portions and stirring continued at 10° C. for 30 minutes, then at room temperature for 2 hours. The reaction mixture was poured on cold saturated aqueous ammonium chloride and thoroughly extracted with ethyl acetate (6×100 ml). The combined organic layers were washed with brine, dried over sodium sulfate, concentrated and dried in vacuo. The residue was triturated with hexane, filtered and the solid dried. Yield: 51.0 g of 4-hydroxy-8-methoxy-1-(tetrahydro-furan-2-yloxy)-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound P2ii.18) as a tan solid, mp 144-146° C.

Aufarbeitung

  1. waitat room temperature for 2 hours
  2. extractionthoroughly extracted with ethyl acetate (6×100 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customdried in vacuo
  7. customThe residue was triturated with hexane
  8. filtrationfiltered
  9. customthe solid dried

Quellen und Nachweise

ORD-Eintrag
ord-ed581916c85b42d891e8edc38a986ea0
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018135B2

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