Sodium Acetate → 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester

HRID 1034264Notizen

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Reaktionsgleichung von HRID 1034264
[C:1]([S:5][CH2:6][C:7](=O)[CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].CC([O-])=O.[Na+].Cl.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)N)=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.CC(O)=O>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][N:31]2[C:28]3[C:27](=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=3)[C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:7]2[CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:35][CH:36]=1

Komponenten

6

Edukt 3

HCID 517045Sodium AcetateHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoateHCID 189475691-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

Produkt 1

HCID 117625003-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 39 g methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate (Ketone 2) in a mixture of toluene (300 mL) and HOAc (150 mL) was added NaOAc (15 g) and 1-(4-methoxyphenyl)-1-(4-chlorobenzyl)-hydrazine hydrochloride (50 g). The reaction was stirred at r.t. for 3 days under argon in the dark. The mixture was poured onto H2O (1 L) and extracted with 3× EtOAc (500 mL). The EtOAc was washed with 3× H2O (500 mL) then once with NaHCO3 solution. The organic phase was dried (MgSO4), evaporated to dryness, and the residue crystallised from Et2O/hexane 2:1 to afford the title compound; m.p. 102°-103° C.

Aufarbeitung

  1. additionThe mixture was poured onto H2O (1 L)
  2. extractionextracted with 3× EtOAc (500 mL)
  3. washThe EtOAc was washed with 3× H2O (500 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated to dryness
  6. customthe residue crystallised from Et2O/hexane 2:1

Quellen und Nachweise

ORD-Eintrag
ord-8e41235a655c422f92853fe9ba6ac6e7
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05314898

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