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Sodium hydride → Methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-nitrobenzyl)amino]propionate

HRID 1420590
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1420590
[OH:1][CH2:2][CH:3]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[N+:22]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br)([O-:24])=[O:23]>CN(C)C=O.C(OCC)(=O)C.O>[OH:1][CH2:2][CH:3]([N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[N+:22]([O-:24])=[O:23])[C:4]([O:6][CH3:7])=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotolueneHCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

Produkt 1

HCID 18612897Methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-nitrobenzyl)amino]propionateAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 15.0 g (51.85 mmol) of methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate in 125 ml of N,N-dimethylformamide, cooled in an ice bath, was added portionwise 2.29 g (57.03 mmol) of NaH (60% in oil). The mixture was stirred at 0° C. for 20 minutes and then a solution of 12.32 g (57.03 mmol) of 2-nitrobenzyl bromide in 25 ml of dry N,N-dimethylformamide was added dropwise. The solution was stirred at room temperature for 48 hours and diluted with 500 ml of ethyl acetate and water. The organic layer was separated and the aqueous layer extracted with 250 ml of ethyl acetate. The combined organic layer and extract was washed with 200 ml each of H2O, 1 N NaHCO3, brine and dried with Na2SO4. The solvent was removed and the residual solid was triturated with ethyl acetate, cooled and filtered to give 13.5 g (61%) of white crystals, having a m.p. 127-129° C. From a small scale run (3.0 g) there was obtained 2.32 g of white crystals, having a m.p. 127-129° C. Anal. for C18H20N2O8S: Calc'd: C.50.9; H,4.8; N,6.6; Found: C,50.9; H,4.8; N,6.5.

Aufarbeitung

  1. stirringThe solution was stirred at room temperature for 48 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with 250 ml of ethyl acetate
  4. extractionThe combined organic layer and extract
  5. washwas washed with 200 ml each of H2O, 1 N NaHCO3, brine
  6. dry with materialdried with Na2SO4
  7. customThe solvent was removed
  8. customthe residual solid was triturated with ethyl acetate
  9. temperaturecooled
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-4e1795c898c94f4db97dc8c16b330e7f
Quelldatensatz
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06071903

Notizen zur Reaktion

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