Trifluoroacetic acid → Methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)benzoate

HRID 715969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 715969
FC(F)(F)C(O)=O.[Br:8][C:9]1[C:14]([CH2:15][CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2C(OC(C)(C)C)=O)=[C:13]([C:29]([O:31][CH3:32])=[O:30])[C:12]([NH:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:11][CH:10]=1>C(Cl)Cl>[Br:8][C:9]1[C:14]([CH2:15][CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)=[C:13]([C:12]([NH:33][C:34](=[O:39])[C:35]([CH3:37])([CH3:38])[CH3:36])=[CH:11][CH:10]=1)[C:29]([O:31][CH3:32])=[O:30]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 70982387Tert-butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate2×

Produkt 1

HCID 70982675Methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)benzoateAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (15 mL) was added to a solution of tert-butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate (Intermediate 36, 2.54 g) in DCM (15 mL) and the mixture was left to stand at room temperature for 30 minutes. The resultant solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and potassium carbonate solution. The organic layer was dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo to give methyl 3-bromo-6-(2,2-dimethylpropionylamino)-2-(2-pyrrolidin-2-yl-ethyl)benzoate (2.05 g) as a white foam.

Aufarbeitung

  1. waitthe mixture was left
  2. concentrationThe resultant solution was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and potassium carbonate solution
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1e5ba14e7ac04c6eaead59af8e7f7eee
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187494B2

Notizen zur Reaktion

Wird geladen…