Trifluoroacetic acid → 3-methyl-4-{[(3R)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile

HRID 2066103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066103
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[C@H:14]([CH3:25])[CH2:13]2)(=[O:11])=[O:10])=[C:5]([CH3:26])[CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[CH3:26][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[S:9]([N:12]1[CH2:17][CH2:16][NH:15][C@H:14]([CH3:25])[CH2:13]1)(=[O:11])=[O:10])[C:1]#[N:2]

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 591613281,1-dimethylethyl (2R)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate

Produkt 1

HCID 591613863-methyl-4-{[(3R)-3-methyl-1-piperazinyl]sulfonyl}benzonitrileAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl (2R)-4-[(4-cyano-2-methylphenyl)sulfonyl]-2-methyl-1-piperazinecarboxylate (may be prepared as described in Description 19) (3.24 g, 8.54 mmol) and TFA (7.00 ml, 91.0 mmol) in dry DCM (10 ml) was stirred at rt for 1 h, then concentrated under vacuum, azetroping with toluene (25 ml) to give an orange oil. This was redissolved in MeOH (10 ml) then applied to an SCX-2 cartridge (50 g), washing with MeOH. The product was eluted with 2M NH3 in MeOH; concentration under vacuum gave the title compound as a pale orange oil (8.17 mmol).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customto give an orange oil
  3. washwashing with MeOH
  4. washThe product was eluted with 2M NH3 in MeOH
  5. concentrationconcentration under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-02348916af644f7584c6d34bba702f56
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288388B2

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