Ammonium Chloride → 4-(2-Chlorophenyl)-2-methyl-6-(2-oxo-ethoxymethyl)-1,4-dihydro-3,5-pyridinedicarboxylic acid 5-ethyl 3-methyl ester

HRID 1250

Reaktionsgleichung

Reaktionsgleichung von HRID 1250
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:8]([CH2:12][O:13][CH2:14][CH:15]([OH:18])CO)[NH:9][C:10]=1[CH3:11])=[O:4].I([O-])(=O)(=O)=O.[Na+].[Cl-].[NH4+]>CO.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:8]([CH2:12][O:13][CH2:14][CH:15]=[O:18])[NH:9][C:10]=1[CH3:11])=[O:4]

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 23667635Sodium periodateHCID 698316324-(2-Chlorophenyl)-2-(2,3-dihydroxypropoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

Produkt 1

HCID 867521804-(2-Chlorophenyl)-2-methyl-6-(2-oxo-ethoxymethyl)-1,4-dihydro-3,5-pyridinedicarboxylic acid 5-ethyl 3-methyl esterAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of 4-(2-chlorophenyl)-2-(2,3-dihydroxypropoxymethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (IC, 13.0 g) in methanol (150 mL) was added a solution of sodium periodate (7.6 g) dissolved in water (100 mL) dropwise over 15 min. After stirring for 10 min, a saturated solution of ammonium chloride (25 mL) was added. Volatile materials were removed under reduced pressure, then ethyl acetate (200 mL) and water (100 mL) were added. The organic layer was separated and the aqueous layer was twice extracted with ethyl acetate (50 mL). The combined organic fractions was washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo to afford the title compound (11.8 g). Thin layer chromatography and proton NMR spectrum showed the crude title compound (ID) was sufficiently pure.

Aufarbeitung

  1. customVolatile materials were removed under reduced pressure
  2. additionethyl acetate (200 mL) and water (100 mL) were added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was twice extracted with ethyl acetate (50 mL)
  5. washThe combined organic fractions was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-df519091f55147ec9c9c3a495aefb74e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723618

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