Trifluoroacetic acid → methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate

HRID 595113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595113
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[C:14]([O:15][CH2:16][CH:17]2[CH:21]=[CH:20][CH2:19][N:18]2C(OC(C)(C)C)=O)=[C:13]([C:29]([O:31][CH3:32])=[O:30])[C:12]([N:33](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:33][C:12]1[C:13]([C:29]([O:31][CH3:32])=[O:30])=[C:14]([O:15][CH2:16][CH:17]2[CH:21]=[CH:20][CH2:19][NH:18]2)[C:9]([Br:8])=[CH:10][CH:11]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86712822Tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate2×

Produkt 1

HCID 86712821methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoateAusbeute 88,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TFA (5 mL) was slowly added to a suspension of tert-butyl 2-(6-bromo-3-[bis-(tert-butoxycarbonyl)amino]-2-methoxycarbonylphenoxymethyl)-2,5-dihydropyrrole-1-carboxylate (Intermediate 19, 3.55 g) in DCM (5 mL). The resultant dark solution was stirred at room temperature for 3 hours. The volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution. The layers were separated and the aqueous layer was extracted with more ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate (1.64 g) as a dark oil.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with more ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fd2e6b58ce0f43baa74117bcaa278b47
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242997B2

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